155197-37-8Relevant articles and documents
A direct method for β-selective glycosylation with an N-acetylglucosamine donor armed by a 4-O-TBDMS protecting group
Tanaka, Hidenori,Hamaya, Yu,Kotsuki, Hiyoshizo
, (2017)
A new direct method for β-selective glycosylation with an N-acetylglucosamine (GlcNAc) donor was developed. This substrate, which can be readily prepared from commercially available GlcNAc in two steps, contains a 4-O-tert-butyldimethylsilyl (TBDMS) protecting group as a key component. We found that this functionality could have a favorable effect on the reactivity of the GlcNAc donor. Glycosylation with the armed donor using primary alcohols in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate (TMSOTf) in 1,2-dichloroethane smoothly gave the desired coupling products in good yields with complete β-selectivity, while sterically hindered acceptors were less efficient.
New procedure for the preparation of 2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside and other alkyl β-glycosides
Sowell, C. Gregory,Livesay, Mark T.,Johnson, David A.
, p. 609 - 610 (2007/10/02)
The title compound and other alkyl β-glycosides 1a-g can be prepared in one step from commercially available 2-acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3) and simple alcohols using camphorsulfonic acid as a promoter together with azeotr
NEW METHOD FOR THE SYNTHESIS OF 2-METHYLGLYCO-2-OXAZOLINES FROM ANOMERIC MIXTURES OF THE PERACETATES OF AMINOSUGARS
Pertel', S. S.,Chirva, V. Ya.
, p. 867 - 869 (2007/10/02)
2-Methylglyco-2-oxazolines, which are reagents for the synthesis of 1,2-trans-N-acetylhexosaminides from the anomeric mixture of aminosugar acetates, are formed from the peracetates of aminosugars by the action of a Lewis acid in the presence of a