GlycoNAVI: CheGly (Chemical Glycosylation)

Leaving Group

CheGly
thiourea
trichloroacetimidate
Ac
F
I
UDP
TMS
(1-phenyltetrazol-5-yl)thio droup (ST)
-C(=NPh)-CF3
-C(NH)CCl3, OAc
-CO2R
-O-C(=N-p-CF3Ph)(S-p-CF3Bn)
-O-C(=N-p-CF3Ph)(S-p-CF3Bn), trichloroimidate, F
-O-C(=NH)-CF3
-O-C(=NPh)-CF3
-O-C(=NPh)-CF3, S(O)Et
-O-C(=NPh)-CF3, trichloroimidate
-O-C(O)-N(R)(Ts) Glycosyl Sulfonylcarbamates
-O-C(O)-OPh
-O-C(O)-OPh(or Me)
-O-C(O)-S-(2-Py)
-O-C(S)-N-imidazole
-O-CH(=NMe2)+
-O-P(=NPh)(NiPr2)(OEt)
-O-P(=NPh)-(OEt)2
-O-P(=NPh)-(OEt)2, -O-P-(NiPr2)(OEt)
-O-P(=NTs)-Ph2
-O-P(=O)(OPh)2
-O-P(=O)-(NMe2)2
-O-P(=O)-(OBu)2
-O-P(=O)-(OCH2)2CH
-O-P(=O)-(OPh)2
-O-P(=O)-(OR)2
-O-P(=O)-F2
-O-P(=S)(OMe)2
-O-P(OEt)2
-O-P-(NiPr2)(OEt)
-O-P-(OBn)2
-O-P-(OCH2CCl3)2
-O-P-(OEt)2
-O-P-(OMe)2
-O-P--(OEt)2
-O=P(=S)-Me2
-OC(=NH)CCl3
-OC(NH)CCl3
-OC(NPh)CF3
-OC(O)(CH2)3CC
-OP(O)OBu2, -C(NH)CCl3
-OP(OEt)2
-OSO2CF3
-S(NTs)Et
-S(O)Et
-S-C(O)-OPh
-S-C(S)-NEt2
-S-C(S)-NEt2, -S-C(S)-OEt
-S-C(S)-OEt
-S-C(S)-piperidine
-S-P(=NPh)-(NMe2)2
-S-P(=S)(OMe)2, -S-P(=S)(O-CH2)2-C-Me2
-S-P(=S)-(O-CH2)2-C-Me2
-S-P(=S)-(OEt)2
-S-P(=S)-(OMe)2
-S-S-Et
-S-S-Me
-SC(S)NEt2
1,2-cyclic thiocarbonate
1-Hydoroxy Sugar
1-OH sugar, trichloroimidate, OAc, F
1-thioimidoyl
1-tributylstannyl glycals
2'-caboxybenzyl glycoside
2,4-Dichloro-1,3,5-triazinyl glycoside
2-Allyloxyphenyl glycoside
2-PyS, 2-Pym-S
2-mercaptobenzothiazolyl
3',4'-dimethoxybenzyl glycoside
3'-methoxy-2'-pyridil glycoside
3-Nitro-2-pyridyl (3NPy) glycosides
3-methoxypyridines (MOP)
3-nitro-2-pyridyl and 5-nitro-2-pyridyl glycosides
4-pentenyl Glycoside
4-pentenyl glycoside
6-nitro-2- benzothiazolyl glycoside
?
Alkyloxytris(dimethylamino)phosphonium salts
BocO
Br
Br or Cl
Br, SMe
Br, 2,6-MePhS
Br, Cl
Br, Cl, SPh
Br, F, trichloroimidate, SPh
Br, I
Br, p-NO2PhCOO-
C(S)SMe
COC6H4-p-NO2
COCCl3
COCF3
Cl
Cl, Br
Cl, F
Cl, OP(OEt2), Br, SEt
Dicyclohexylmethyl thioglycosides
F, OAc
F, S(O)Ph
F, SEt
F, trichloroimidate
Glycosyl Samarium(III)
Glycosyl bomide or Chloride
Glycosyl-N-allyl carbamates
Hg
I, trichloroacetimidate
N-(4-methoxyphenyl)-trifluoroacetimidate
N-Glycosyl Triazoles
N-methylacetimidoyl
N-phenyltrifluoroacetimidate
N-trichloroacetylcarbamate
N-unsubstituted, mono-, disubstituted carbamates
OC(=NH)CCl3, PTFAI(N-Phenyl trifluoroacetimidates), OFox(3,3-difluoro-3H-indol-2-yl)
OAc
OAc, COCH2Br
OAc, OC(O)CH2Cl
OBz
OC(=NPh)CF3, SPh
OC(NPh)CF3
OC(O)Me
OC(O)Ph
OCOC6H4-o-CO2Bn(benzyl phthalate)
OCOCH2I
OCOCH2OC2H4OMe
OCOCH2OMe
OCOPy
ODMPM
OH
OH or OMe
OH, OAc, -C(NH)CCl3
OMe
OSO2(2-CF3Ph)
OSPh2
OTMS
OTs
OpNP (p-nitrophenyl)
PhS(O)
PhS(O)-
PhS(O)-, F
PhS(O)-, SePh
PhS(O)2-
Propargyl Glycosides
S(CH2)2CCH
S(O)Ph
S(O)Tol, STol
S-2-thiazolinyl
S-Benzimidazolyl
S-Ph-pX (X=EDG; H, Me, OMe, NHAc)
S-Php-O-C8H17
SAr
SBox
SBox, STaz
SCN
SCN, SEt, STaz, SBox
SEt
SEt, -C(NH)CCl3, F, S(O)Ph
SEt, OCNCCl3
SEt, S(O)Et
SEt, SBox
SEt, SMe, SPh
SEt, SPh
SEt, SPh, STol, S/O-imidates
SEt, dicyclohexylmethyl thioglycosides
SEt, trichloroacetimidate
SMe
SMe, Br
SMe, F
SMe, SEt
SMe, SEt, SPh
SMe, SPh
SMe, SPh, SEt
SO2Ph
SO2Py
SPMP
SPh
SPh or OAc
SPh, -C(NH)CCl3, S-2,6-MePh
SPh, F
SPh, OCO(NPh)CF3
SPh, PhS(O)OMe, PhS(O), SPhCl2
SPh, S(O)Et, S(O)Ph
SPh, SBu
SPh, SMe
SPh, SOEt
SPh, SPMP
SPh, SPy
SPh, SR, SPh-4-OMe
SPhCl
SPhMe
SPr
SPy
SR
SR (R = ?)
SR (R= ?)
STaz
STaz, SEt
STol
STol, -C(NH)CCl3
STol, S(O)Tol
SePh
SePh, alkyl thio-, phenyl thio-
SnBu3
Sp-NOPh
Spy
TBS
Telluruoglycoside
Thiazolylketoses
allyl glycoside
allylic phosphates
azid
diazide
diphosphonium salt
enol ether
enol ether and imidates
enol ether, OC(O)OC(=CH2)CH3
Synthesis of the Blood Group Antigens Lea, Leb, and Lex Using a Standard Set of Reaction Conditions
glycosyl bromides and phenylthio glycoside
glycosyl pyridyl sulfones
glycosylthio, glycosyldithio, selenophosphates
isopropenyl glycoside
methyl dinitrosalicylate (DISAL)
n-Pentenyl
n-pentenyl
n-pentenyl franoside
n-pentenyl glycoside
n-pentenyl, SEt
nBu3Sn
nBuSn
o-cyclopropylethynylbenzoates
o-hexynylbenzoate
o-nitrophenyl
ortho-alkynylbenzoates
ortho-hexynylbenzoate
ortho-hexynylbenzoates
trichloroimidate, -O-P-(OEt)2, 4-pentenyl Glycoside, 1,2-orthoester
p-nitrophenyl
pentenoate
phosphite and phosphate
propargyl glycosides
propargyl glycosides OCH2CCR (R = H, Me)
pyS(O)2-
pyridylsulfone
sulfoxide
tetrazole, -OP(OEt)2
tributylstannyl
trichloroacetimidate, F
trichloroacetimidate, F, thioglycoside
trichloroacetimidate, OP(O)OBu2
trichloroacetimidates
trichloroacetimidates, thioglycosides
trichloroacetylcarbamate
trichlorocarbamate, trichloroacetate
trichloroimidate
trichloroimidate (or C(=NPh)-CF3)
trichloroimidate, -O-C(=NPh)-CF3
trichloroimidate, OAc
trichloroimidate, SPh, F
trichloroimidate, alkylsulfenyl, halide
trifluoroacetimidate
n-Pentenyl ortho esters (NPOEs), n-pentenyl glycosides (NPGs)
-O-CH(=NMe2)+, O-CH(=N(iPr2))+, -O-CH(N-Formylmorpholine)
-O-C(=N-Ph)(SCF3)? ?
2_Deoxy-Sugars
glycosylthio heterocycles(SPy,?SQu,?SIm,?STh,?SBth,?SBox,?STr,?SOxd,?SThd,?STe,?SPd,?SPm,?SPz,?SQz,?SBtz,?SQx,?STz)
Dichloro?]cyanoacetimidates
F?H
F?H(Cl?)
S-Box? (S-benzoxazolyl)
S-Box? (S-benzoxazolyl), S-Benzimidazolyl
SAda?(1-adamantanylthio)
diazirine sugar via glycosylidene carbene?
isopropenyl, n-pentenyl ?glycoside
isopropenyl?glycoside