161016-86-0

Upstream product

• 100-39-0 benzyl bromide 
• 134039-06-8 methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside 
• 191485-91-3 Trifluoro-methanesulfonic acid (2R,3S,4R,5R,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yl ester 
• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 
• 51842-16-1 methyl 2,3,6-tri-O-benzyl-β-D-galactopyranoside 
• 53685-11-3 methyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 528861-64-5 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone 

Downstream Products

• 192372-92-2 methyl 2,3,6-tri-O-benzyl-5-C-methoxy-α-L-idopyranoside 
• 192372-91-1 methyl 2,3,6-tri-O-benzyl-5-C-methoxy-β-D-glucopyranoside 
• 528861-64-5 1-{methyl (4S,5R)-2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hexopyranosid[4,5-b]-2-methyl-1,4-oxathiin-3-yl}ethanone 

Relevant academic research and scientific papers

Regiospecific synthesis of 4-deoxy-D-threo-hex-3-enopyranosides by simultaneous activation-elimination of the talopyranoside axial 4-OH with the NaH/Im2SO2 system: Manifestation of the stereoelectronic effect

A new and high-yielding method for the regioselective preparation of 4-deoxy- and 2,4-dideoxy-2-acetamido-β-D-threo-hex-3-enopyranosides has been developed. The process involves a simultaneous activation-elimination of the OH-4 group of β-D-talopyranoside

Conformational evaluation of some 4-deoxyhex-4-enopyranose derivatives and their use in the preparation of a previously undescribed class of 3-thio-L-sorbopyranosides and their 6-C-methoxy analogues

A new series of thio-substituted sugars were synthesised relying on the totally regio- and stereoselective cycloaddition of 4-deoxyhex-4-enopyranose derivatives to 'in situ' generated oxothiones. Conformational studies of the above unsaturated sugars showed a marked prevalence of the all-axial conformer.

An efficient and highly regioselective synthesis of 4-deoxy- and 2-acetamido-2,4-dideoxy-β-D-threo-hex-3-enopyranosides

The preparation of the previously undescribed class of 4-deoxy- and 2,4-dideoxy-2-acetamido-β-D-threo-hex-3-enopyranosides was accomplished with a very high yield and a complete regioselectivity by means of a simultaneous activation-elimination process of

Synthesis of methyl 4-thio-β-cellobioside. A reinvestigation

The best yield for the synthesis of the title compound was obtained by nucleophilic displacement of the di-O-triflyl group in methyl tri-O-benzyl-4-O-triflyl-β-D-galactopyranoside by 2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thio-β-D-glucopyranose in HMPA in the presence of diethylamine. Under these conditions, the formation of unsaturated side products was decreased.

A new route to D-xylo-hexo-5-ulose and some of its selectively protected derivatives from D-galactose(

A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl β-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-eno