552
3
Chemical Glycosylation Reactions
⊡ Table 3
Glycosylation with 1-O-carbonates and related sugars
References
X
Activator
Me 2 SiCl 2 /AgClO 4 , TrB(C 6 F 5 ) 4
[48,73,74,75]
TMSOTf
[76]
ZnBr 2
[77]
IDCP
[78]
TMSOTf
[79]
AgOTf
[80,81]
⊡ Scheme 62
(Ref. [48])
and coworkers showed the high-yielding β-stereoselective glycosylation employing glucosyl
isopropenylcarbonate as the glycosyl donor ( > Scheme 65) [76].
Ley and Ford reported the C-1 (1-imidazolylcarbonyl) glycosides as new glycosyl donors,
which reacted with a series of alcohol acceptors in the presence of ZnBr 2 to give the corresponding O-glycosides ( > Scheme 66) [77]. Kunz and Zimmer reported the N-allyl carbamate as an anomeric leaving group with soft electrophiles, for example, IDCP, DMTST,
and methyl bis-methylthiosulfonium hexachloroantimonate, as promoters for the O-glycoside
synthesis ( > Scheme 67) [78]. Kiessling and Hinklin reported glycosyl sulfonylcarbamates
3
Chemical Glycosylation Reactions
⊡ Table 3
Glycosylation with 1-O-carbonates and related sugars
References
X
Activator
Me 2 SiCl 2 /AgClO 4 , TrB(C 6 F 5 ) 4
[48,73,74,75]
TMSOTf
[76]
ZnBr 2
[77]
IDCP
[78]
TMSOTf
[79]
AgOTf
[80,81]
⊡ Scheme 62
(Ref. [48])
and coworkers showed the high-yielding β-stereoselective glycosylation employing glucosyl
isopropenylcarbonate as the glycosyl donor ( > Scheme 65) [76].
Ley and Ford reported the C-1 (1-imidazolylcarbonyl) glycosides as new glycosyl donors,
which reacted with a series of alcohol acceptors in the presence of ZnBr 2 to give the corresponding O-glycosides ( > Scheme 66) [77]. Kunz and Zimmer reported the N-allyl carbamate as an anomeric leaving group with soft electrophiles, for example, IDCP, DMTST,
and methyl bis-methylthiosulfonium hexachloroantimonate, as promoters for the O-glycoside
synthesis ( > Scheme 67) [78]. Kiessling and Hinklin reported glycosyl sulfonylcarbamates