GlycoNAVI: CheGly (Chemical Glycosylation)

Leaving Group

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