91510-87-1

Upstream product

• 18292-38-1 2-methallyltrimethylsilane 
• 3879-79-6 (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 67883-62-9 2-methylallyltributyltin 
• 91602-61-8 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α/β-D-glucopyranoside 

Relevant academic research and scientific papers

8-(Methyltosylaminoethynyl)-1-naphthyl (MTAEN) Glycosides: Potent Donors in Glycosides Synthesis

With 8-(methyltosylaminoethynyl)-1-naphthyl (MTAEN) glycoside as donors, a novel and efficient glycosylation protocol has been established. The MTAEN glycosylation protocol exhibits the merits of shelf-stable donors, mild catalytic promotion conditions, considerably extended substrate scope encompassing both free alcohols, silylated alcohols, nucleobases, primary amides, and C-type nucleophile acceptors, and applicability to various one-pot strategies for highly efficient synthesis of oligosaccharides, such as orthogonal one-pot, single-catalyst one-pot, and acceptor reactivity-controlled one-pot strategies.

STEREOSELECTIVE SYNTHESIS OF 3-(D-GLYCOPYRANOSYL)PROPENES BY USE OF ALLYLSILANES

Reactions of allylsilanes with methyl pyranosides and pyranosyl chlorides proceeded very smoothly in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate and iodosilane to give the corresponding glycopyranosyl-3-propenes in highly stereoselective mode.The configuration depends upon the structure of allylsilanes. 2-Bromo-2-propenyltrimethylsilane, the lowest nucleophile among the allylsilanes used, afforded an almost pure C-α-glycosyl compound.

TWO NEW METHODS FOR THE SYNTHESIS OF C-GLYCOSIDES

Thiophenyl glycosides are converted to C-glycosides by reaction with allyl or methallyltri-n-butylstannane using both "one-electron" and "two-electron" procedures, which give different stereoselectivities in some cases.

HIGHLY STEREOSELECTIVE C-ALLYLATION OF GLYCOPYRANOSIDES WITH ALLYLSILANES CATALYZED BY SILYL TRIFLATE OR IODOSILANE

Methyl α-D-glucopyranoside, methyl α-D-mannopyranoside and, in particular, the corresponding α-D-glycopyranosyl chlorides readily undergo allylation with allylsilanes catalyzed by trimethylsilyl triflate or iodotrimethylsilane in a highly stereoselective mode.