GlycoNAVI: CheGly (Chemical Glycosylation)

promoter

CheGly
TMSOTf
Tf2O, DTBMP
Tf2O, TTBP
Tf2O, TBP
Ph2SO-Tf2O
PhIO-Tf2O
TTBP-Tf2O
SO2Cl2-TfOH
MPBT-Tf2O
TrClO4 (cat)-TMSOTf
n-Bu2SO/TMSOTf
TMSOTf(cat.), SiF4(cat)
BF3?EEt2O/TMSOTf
N-(p-methylphenylthio)-??-caprolactam-TMSOTf
TMSCIO4-(CCl3CO)2O
TMSI-(C4H8N)3P=O
TMSI-Ph3P=O
TMSI-(pyrrolidine)3P=O
TMSI-(Me2N)3P=O
TMSI-(N-Morpholinyl)3P=O
TMSI-Ph3P=S
TMSI-Ph2P(=O)OPh
TMSI-n-Bu3P=O
TMSI-Ph2P(=O)Me
TMSI-(p-MeOPh)3P=O
DEAD-Ph3P
(TMS)3SiH, AIBN
TBAI-DIPEA
TBAI-DIPEA, reflux
BF3 _ Et2O-DTBMP
BF3?EEt2O, TMSOTf
BF3?EOEt2, p-TsOH
HClO4?ESiO2
Trichloroisocyanuric acid (TCCA)_TMSOTf
Me2S2-Tf2O
benzenesulfinyl morpholine, Tf2O
TrB(C6F5)4, PhthNSEt
TrClO4, I2
TrClO4-TMSOTf
MeOTf, 2,6-lutidine
DMTST, Bu4NBr
Tf2O, 1-benzenesulfinyl piperidine
Tf2O, base
KHMDS, Ts2O
TfOH/TEP
I2/Et3SiH
(p-NO2Ph)(Ph)SO, Tf2O
LPTS(2,6-lutidinium p-toluenesulfonate)-nBu4NI
LPTS-nBu4NI
DTPBI-TBAI
Br2/TMSOTf
TsCl,?Bu4N+Cl-
IBr-TfOH
ICl-TfOH
PhIO-TfOH
PhIO-TMSOTf
Me2(MeS)S+OTf- and Bu4N+Br-
TMSOTf-PhSEt
TMSOTf (cat.)
TMSOTf-thiophene
HF-pyridine complex
NaH, decyl trifluoromethanesulfonate
I2/Et3N
polymer bound triarylphosphane-iodine complex and imidazole
CBr4, PPh3, N,N-tetramethylurea(TMU)
CBr4, PPh3
Me3OBF4, 4-Me-DTBP
MeOTf, DTBP
MeOTf-TrClO4
DMTST-DTBMP
1-benzenesulfinylpiperidine-Tf2O
Br2, silver silicate
TBAB, K2CO3
NaH, DMDO
KOt-Bu, I2
PPh3-DEAD
PPh3-DIAD
BSM-TTBP-Tf2O
BSM-Tf2O (additive: TTBP)
BSP-Tf2O-TTBP
Ph2SO-TTBP-Tf2O?
Ph2SO-Tf2O-TBP
Me2S-Tf2O-TTBP
nBu2S=O/(PhSO2)2O/TTBP
CBr4/PPh3/DMF
CuCl2/dppf/AgClO4
NIS-I2-TMSOTf
TrB(C6F5)4+ I2+ DDQ
Ph3PAuOTf, BF3_Et2O and DBU
AgOTf-PhSCl-DTBMP
Phthalic anhydride-DBU-Tf2O
R3P=O (R=aryl, nBu, cyclohexane, (CH2)15CH3), Tf2O, amine
MsOH-CoBr2-R'4NBrX (R'=Et, Bu; X=Br, ClO4)
Me3SiBr, CoBr2, n-Bu4NBr
nBu3P=O-Tf2O-iPr2NEt
Ph2Sn=S-Tf2O-CsF
TMS2O-CaSO4-Sn(OTf)2
TMS2O-CaSO4-Yb(OTf)3
TMS2O-CaSO4-La(OTf)3
TMS2O-CaSO4-SnCl2
TMSCl-Sn(OTf)2-LiClO4
TMSBr-Sn(OTf)2-LiClO4
TMSOCOCF3-Sn(OTf)2-LiClO4
TMSOTf-Sn(OTf)2-LiClO4
TMS2O-Sn(OTf)2-LiClO4
(Ph3P)3RhCl/BuLi/TMSOTf
(Ph3P)3RhCl-DABCO-TMSOTf
TMSOTf(cat)-Ph2Sn=S-LiClO4
TMSI-n-Bu4NI-(i-Pr)2NEt
Pd(OAc)2-Ag2CO3-PPh3
1,3,5-Trimethoxybenzene,Tf2O, DTBMP
Ni(COD)2/Zn, (R)-Ph-pyBox
[Ru(bpy)3]2+, Visible light, amine reductant
AgClO4-SnCl2-di-tert-butylpyridine
DAST-Sn(OTf)2-Bu4NClO4-TEA
NsCl-AgOTf-Et3N-DMA(N,N-dimethylacetamide)
NosCl-AgOTf-Et3N-DMA(N,N-dimethylacetamide)
[1,2-benzenediolato(2-)-O,O']oxotitanium-Tf2O-CsF-iPrNEt
[1,2-benzenediolato(2-)-O,O']oxotitanium-Tf2O-Base
(C4H8N)3P=O
2,6-lutidine
Br_nsted acid (chiral organic cat.)?
BrCCl3, HFIP, blue LED(cat)
DDQ
NMP(1-methyl-2-pyrrolidinone ),?? 40?|60 ??C
Et3N
organolithiums
Bu4NHSO4
9-borabicyclo[3.3.1]nonyl trifluoromethanesulfonate (9-BBN_CF3SO3)
chiral phosphoric acid
1,4-Dicyanonaphthalene (DCN)/h??
NHTf2
MSB or MST
BTIB
selectfluor(1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate))
N-(phenylthio)-??-caprolactam
TBPA
CCl3CHO
2-fluoro-l-methylpyridinium tosylate
DMF
(Ph)2SO
1,3-dithian-2-ylium tetrafluoroborate
NISac(N-Iodosaccharin)
Ph-S-O-SO2CF3(benzene sulphenyl triflate; BST)
Bu4NOTf
HF-pyridine
Me3SiClO4
Me3SiOTf
N-phenylselenophthalimide(NPSP)
secondary amine, Cs2CO3
imidazole(DMAP)??Bu3SnH, reflux??HF(nBu4NF)
AgOTf-lutidine; TMSOTf
AgOTf; NIS-TfOH
TBPA+?E(radical)
h??, TPT(triphenyltin?)
h??
Bu3SnAll, h??
DDQ,??long-wavelength UV, (p-OMe)PhB(OH)2
IPy2BF4
(Ph3P+)2O-2TfO-
Li naphthalenide
N,N-dimethyl-carbamoylmethyldimethylsulphonium chloride
Ph3C+ClO4-
Iodonium-ion
[bmim][OTf] (ionic liquid promoter)
[R4N] [AOT]? (ionic liquid promoter), NIS
e
e- (Bu4NBF4)
e- E = 1.8~2.1 V
Eox = 0.90V, Ag/AgCl, electrolyte: LiClO4 or Bu4NBF4
electrolyte, catalytic amount of NaOTf
Me2S
Bu4NOTf, R1SR2
thermal condition (110?`120??)
thermal condition (140??)
thermal condition (60 or 160??)
??
40?|60 ??C
LiClO4, microwave, 100degree
catalyst: Et3N+BnBr- acceptor: ROH (R=aryl)
catalyst: Et3N+BnCl- acceptor: ROH (R=aryl)
catalyst: Me(CH2)15N+Me3Br- acceptor: ROH (R=aryl)
catalyst: Bu4N+Br- acceptor: ROH (R=aryl)
catalyst: Bu4N+HSO4- acceptor: ROH (R=aryl)
catalyst: Aliquat336 acceptor: ROH (R=alkyl)
catalyst: BuN+Bu3Cl- acceptor: ROH (R=aryl)
Bu4N+Br-
?
BTEAB
TsCl/Bu4N+Cl-
TsCl-TEBA
Trypanosoma cruzi trans-sialidase
Lipase PS-30 from Pseudomonas cepacia
glucosyltransferase (CGTase)
Cellulase
Cellulase,? ??-galactosidase
Lipase
Glycosidase
glycosidase
??-glycosidase from Thermus thermophilus
??-glycosidase from Aspergillus oryzae
??-d-mannanase from Aspergillus niger
Glycosynthase
??-galactosidase from Bacillus circulans
??-galactosidase from bovine testes
??-Galactosidase from Aspergillus oryzae
??-galactosidase
??-d-galactosidase
??-Galactosidase
DBBOTf??
??-galactosidase from Aspergillus niger
??-glucosidase from almond
??-galactosidase from Penicillium multicolor
??-galactosidase from Aspergillus oryzae
??-Galactosidases from Coffea arabica, Aspergillus niger and A. oryzae
??-galactosidase from Talaromyces flavus
thermophilic galactosidase
lipid-coated ??-D-galactosidase
N-acetylhexosaminidase from Aspergillus oryzae
MeOTf
??-N-Acetylhexosaminidase from Aspergillus oryzae
??-N-acetylhexosaminidase
N-acetyl-??-hexosaminidase
sialyltransferase
??2_3-Sialyltransferase
(2??3)-??-sialyltransferase
??2-3-sialyltransferase (ST3Gal-I)
??2-6-sialyltransferase (ST6GalNAc-I)
uridine-5?e-diphospho-galactose 4-epimerase
??(1??3) galactosyltransferase
??-mannosidase from Aspergillus oryzae
??-mannosidase from Helix pomatia
??-glucosidase
glycosyltransferase
galactosyltransferase
??-1,4-galactosyl transferase from bovine colostrum
??-Mannosyltransferase
??-(1??4)-mannosyltransferase
fucosyltransferase
N-acetylglucosaminyltransferase
human-milk (1??34)-??-fucosyltransferase
sucrose synthase and UDP-Glc 4??-epimerase and ??-1,4-galactosyltransferase
Bacillus1,3-1,4-??-D-glucan 4-glucanohydrolases
Lewis ??(1,3/1,4)fucosyltranferase
calf intestinal phosphatase
H4SiW12O40
H3PW12O40
EDCl?EHCl-HOBt (TBTU)
ArS(ArSSAr)+B(C6F5)4-
Volt (+1.5), n-Bu4NClO4
insoluble silver salts
Montomorillonite K-10
Vermiculite
Nafion-H
Microwave, montmorillonite K-10
Amberlyst 15
ACF(carbon? fiber)
4A?AW MS (Acid-Washed Molecular Sieves)
Nafion-TMS
recyclable solid superacid promoter(SO4/ZrO2 ?)
pTSA/[bmim][BF4] ionic liquid
Me4NBr or AgOTf-collidine, pressure of 15 kbar
Ag_NHC complex
silver zeolite
cadmium zeolite
Lawesson reagent
vitamin12a, Zn, NH4Cl
rare earth metal salts, with or without ZnCl2 and Ba(ClO4)2
TsOH or ZnCl2 ?
gold(I)
Acyl Sulfonamide (?⑫?Q??)
TBSOTf
secondary alkyl trifluoromethanesulfonates
TBDMSOTf
gold(I) complex
Pd (0)
palladium
Pd(II)
organocopper
organocuprates
acid promoters
DTBS(OTf)2
enzyme
(CH3)5SiOSO2C4F9
(CH3)3SiClO4
TMSI
thiourea?n
TMSI?or (Me3Si)2, I2
base promoted, acid catalyzed
rhodium(I)
IBr
trichloroacetimidate
ICl
BF3?EEt2O
SmI2?
palladium(II) complex
copper(II)
Iodonium ion
metal trifluoromethanesulfonates
palladium (0)
acid or mercury salt
base catalysis
Pd compound
palladium(0)
titanium(IV)
Tf2O + Lewis acid
Palladium
I2
Br2
NBS
NIS
MeI
DMTST
DTBMP
SiF4
IDCP
DAST
MeSOTf
NOBF4
TrB(C6F5)4 (cat)
TrB(C6F5)4
TrBF4
TrClO4
TrOTf
HB(C6F5)4 or TfOH
HB(C6F5)4
TMSB(C6F5)4
BF3
TBAI
Me3OBF4
SiCl2(OTf)2
SiCl(OTf)3
Pyridinium Triflate (combined with microwave heating )
phenylsulfenyl triflate
LiClO4
LiOTf
Mg(ClO4)2
MgO
Ba(ClO4)2
In
InCl3
InBr3
InI3
InF3
In(OTf)3
AcClO4
AgClO4
AgOTf
TMSOTf and more
AgOTf-DMSO or tetramethylurea or HMPA(catalytic amount)
AgOTf-HMPA(catalyc amount)
Ag2CO3
Ag2O
AgB(C6F5)4
AgPF6
AgBF4
silver tresylate [2,2,2-trifluoroethanesulfonate:Tresylate]
Hf(OTf)4
ZrCl4
Yb(NTf2)3
Cu(OTf)2
CuOTf(C6H6)0.5
CuCl2
CuBr2
CdCl2
AuBr3
AuCl3
Ph3PAuNTf2
Ph3PAuOTf?, ?Ph3PAuNTf2
Ph3PAuOTf
Yb(OTf)3
Tb(OTf)3
Ho(OTf)3
Tm(OTf)3
PhSeOTf
PhSeOTf, thermal condition
Bu3SnH, AIBN
Bu3SnH
Bu3SnSnBu3, h??
SnCl2
SnCl4
SnCl3(ClO4) (cat)
SnCl3(ClO4)
Sn(OTf)2
Sn(OTf)2 (cat)
SnCl2(OTf)2
SnCl3(OTf)
SnBr4
tributylstannyllithium
Methallyltri-n-butylstannane
allyltri-n-butylstannane
ZnCl2
ZnBr2
Zn(acac)2
Zn(Ac)2
Zn(CN)2
Zn(OTf)2
ZnO
(p-tBuC6H4CO2)2Zn
HgCl2
HgBr2
Hg(OBz)2
Hg(OTf)2
Hg(CN)2
PhHgOTf
Sm(OTf)3
SmI2
TiF4 or SnF4
TiF4
TiCl4
TiCl2(OTf)2
Tl(NO3)3
Me2GaCl, Me2GaOTf
[Rh(??)(MeCN)3(triphos)](TfO)3
FeCl3, TMSOTf, BF3?EEt2O, LiClO4
FeCl3
La(ClO4)3?EnH2O (cat)
Ni(4-F-PhCN)4(OTf)2
Bi(OTf)3
Ph3Bi(OTf)2
BiCl3
Et3Al
Me3Al
Pr3Al
i-Bu3Al
Et2AlCCBu
Me2AlCCBu
Me2AlCCSiMe3
Et2AlCN
Et2AlCl2
MoO2Cl2
TrSbCl6
monomethoxyTrSbCl6
lanthanide(III) triflate
Pd(PhCN)2(OTf)2
Pd(CH3CN)4(BF4)2
Pd(ClO4)2
Pd(PhCN)2Cl2/L, L = 2,4,6-tri-iPrPh-[2-P(tBu)]Ph
Pd(Ph3P)4
Pd(Ph3P)2Cl2
Pd(OAc)2
Pd(PhCN)2Cl2
[Pt(C2H4)Cl2]2 Zeise?fs dimer
Pd2(DBA)3
ReOCl3(SMe2)(Ph3PO)
p-Ts2O
TfOH
Tf2O
Tf2O, TfOH
HB(C6F5)4, HClO4, HNTf2 and more
TfOH or HClO4
HClO4(cat)
PPTS
C8F17SO3H (cat)
H3PO4
MeONa
NaH
KH
KOH
HF
n-BuLi
BuLi
Sat. NaHCO3
LDA
Sn(OTf)2-collidine
Sn(OTf)2-TMU
Sn(OTf)2-BF3?EEt2O
Sn(OTf)2/TMSCl
TrCl-ZnCl2
I2-DDQ
Cu(OTf)2-BTF
pTsOH,? BF3?EEt2O
SnCl2-AgClO4
NIS-AgOTf
NIS-In(OTf)3
NIS-Sn(OTf)2
NIS-LiClO4
NBS-AgOTf
NBS-In(OTf)3
CuBr2-Bu4NBr
PhSeNPhth-TMSOTf
PhSeOTf-TTBP
MgBr2?EEt2O
PhIO-Mg(ClO4)2
SO4/ZrO2
Br2-AgOTf
Br2-Ag2CO3
IBr-AgOTf
IBr-In(OTf)3
ICl-AgOTf
ICl-In(OTf)3
PhIO-AgOTf
PhIO-In(OTf)3
SnCl2-TrClO4
Sn(OTf)2-DTBP
(MeO)2P(=S)-S-Br/AgOTf
TMSOTf_AgClO4
TMSOTf?|AgClO4 or TMSOTf
TMSOTf-AgClO4
MeOTf, Cu(OTf)2, or Yb(OTf)2
AgOTf, p-TsSCl
AgOTf-TMSOTf
AgPF6-DTBMP
p-NO2PhSCl-AgOTf
p-TolSCl, AgOTf
FeCl3-I2
CuCl-I2
AgOTf-SnCl2
La(OTf)3-NIS
Cu(OTf)2-NIS
Cu(OTf)2/cat-TfOH
Cu(OTf)2-DMTST
Bromodimethylsulfonium Bromide(BDSM)-AgOTf
MeSiCl3-AgClO4 (cat)
NBS, Bi(OTf)3
TMSCl-Zn(OTf)2
AgF-Ag2CO3
TBPA, (4-BrPh)3NH+SbCl6-
AgOTf-K2CO3
MeSO3H-CoBr2
TrB(C6F5)4-LiClO4
TrB(C6F5)4-LiOTf
TrB(C6F5)4-LiBF4
TrB(C6F5)4-LiNO3 (X: ClO4, I, NTf2)
TrB(C6F5)4-LiI
TrB(C6F5)4-LiNTf2
TrB(C6F5)4-NIS(or NBS)
TrB(C6F5)4-NaIO4
MeOCH2CO2H-Yb(OTf)3
TMSOTf(cat)-Ph2Sn=S
InCl3-TMSCl
Me2SiCl2-AgClO4
MeOSO2F-CaF
CuOAc-DBU
Et2O_ZnCl2
AgOTf, 2,4,6-trimethylPy
Ag2O-Py
TMSOTf-CaCl2
p-TolSl- AgOTf
AgClO4-Lawesson's reagent
[1,2-benzenediolato(2-)-O,O']oxotitanium-TMSOTf
Pd2(dba)3-PPh3
Pd(OAc)2-P(OPh)3
Pd(OAc)2-PPh3
[Co(dmgH)2py]2-NaBH4
NiCl2-ligand, NiCl2-Ligand(PyBox)
?⑫?A?R?????g?Q??
alkyne-Co2(CO)6 complex, TMSOTf
Ti(OtBu)4, mandelic acid
Cp2HfCl2/AgX (X=OTf, ClO4)
SnCl4, PhOSnBu3
AuBr3, AgOTf
(4-CF3Ph)3PAuCl, AgOTf
PhSeNPhth-Mg(ClO4)2
SnCl2-AgOTf
SnCl4-AgClO4 (cat)
SnCl4-AgClO4
SnCl2-SnCl4 (cat)
SnCl4-Sn(OTf)2 (cat)
Sn(OTf)2-LiClO4
AgClO4-LiClO4
Ag2CO3-AgClO4
GaCl3-AgClO4 (cat)
ZnCl2-AgClO4
Bu2SnCl2, Me2SnCl2, Bu3SnCl, Me3SnCl, and Ph3SnCl with AgClO4
Cp2MCl2-AgClO4 (M=Zr or Hf)
Cp2MCl2-AgX (M=Hf, Zr; X=ClO4, OTf)
Cp2HfCl2-AgClO4
Cp2HfCl2-2AgClO4
Cp2HfCl2-AgOTf
Cp2ZrCl2-AgBF4, Cp2HfCl2-AgOTf
Cp2ZrCl2-AgBF4
Cp2ZrCl2-AgClO4
La(ClO4)3?EnH2O-Sn(OTf)2
Bu2SnCl2?%5C2AgClO4
AgClO4-Ph3Sn=S
LnPtMe3BF4, Cu(OTf)2
Pd(MeCN)2Cl2-AgOTf
PdCl2(dppf)-CuCN
Zn/ZnCl2
SnCl2-AgB(C6F5)4
SnCl2-AgB(C6H5)4
Hg(CN)2-HgBr2(1:1 mixture)
Hg(CN)2-HgBr2(1.6:0.5 mixture)
Zn_Cu
CeCl3_Nal
Cu(OTf)2-CuO
NIS-TMSOTf
NIS-TMSOTf, DMF
NIS-TfOH
NIS-TfOH (cat)
NIS-TfOH?in the presence of DTBMP
NBS-TfOH
NIS-TESOTf
NIS-MeOTf
NIS-BF3?EEt2O
NIS, HClO4_silica
NIS, HClO4-SiO2
NIS-Et3SiOTf
NIS-IDCT
NBS-Bu4NOTf
NBS-Ph2IOTf
NBS-TMSOTf
NBS-QOTf
PhSOTf-DTBMP
I2-DTBMP
N-PhS-caprolactam-Tf2O
BSM-Tf2O
BSP/Tf2O
DPS/Tf2O
BSP/DTBMP
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