122672-65-5

Upstream product

• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 
• 105-36-2 ethyl bromoacetate 
• 194149-26-3 methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 
• 73395-15-0 methyl endo(phenyl)-2,3:4,6-di-O-benzylidene-α-D-mannopyranoside 

Downstream Products

• 134622-79-0 methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-allopyranoside 
• 101199-49-9 methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-((ethoxycarbonyl)methyl)-3-C-((Z)-(ethoxycarbonyl)methylene)-α-D-ribo-hexopyranoside 
• 122672-66-6 methyl 4,6-O-benzylidene-2-deoxy-2-C-((ethoxycarbonyl)methyl)-2-C-methyl-α-D-ribo-hexopyranosid-3-ulose 
• 122622-39-3 (2R,4aR,6S,7R,8S,8aR)-7-(2-Hydroxy-ethyl)-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 122592-16-9 ((2R,4aR,6S,7R,8S,8aR)-8-Hydroxy-6-methoxy-7-methyl-2-phenyl-8-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetic acid ethyl ester 
• 122592-17-0 methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2-deoxy-2-C-methyl-3-C-vinyl-α-D-allopyranoside 
• 122622-27-9 methyl 4,6-O-benzylidene-2-C-(2-(tert-butyldimethylsiloxy)ethyl)-2,3-dideoxy-3-C-(formylmethyl)-2-C-methyl-3-C-((E)-1-propenyl)-α-D-allopyranoside 
• 101199-50-2 methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(2-hydroxyethyl)-3-C-((Z)-2-hydroxyethylidene)-α-D-ribo-hexopyranoside 
• 122592-15-8 (2R,4aR,6S,6aR,9aS,9bR)-6-Methoxy-6a-methyl-2-phenyl-9a-vinyl-hexahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxin-8-one 
• 122592-28-3 (10R)-methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methyl-α-D-glucopyranosido<3,2-c>-10-methylbicyclo<3.3.0>octan-11-one 

Relevant academic research and scientific papers

Synthesis of homochiral trisubstituted γ-butyrolactones

Efficient syntheses of homochiral, trisubstituted γ-butyrolactones via the highly stereoselective alkylation of a carbohydrate-derived γ-lactone are described.

General Synthesis of Homochiral Trisubstituted γ-Butyrolactones

The synthetically useful keto ester methyl 2-deoxy-2-(2-ethoxy-2-oxoethyl)-4,6-O-(phenylmethylene)-α-D-ribo-hexopyranosid-3-ulose can be prepared exclusively by reaction of the potassium enolate of methyl 2-deoxy-4,5-O-(phenylmethylene)-α-D-erythro-hexopy

Serial Radical Cyclization of Branched Carbohydrates. 1. Simple Pyranoside Diquinanes

The 2-deoxy-3-ketopyranoside 5 is converted efficiently into two multiply branched derivatives containing functionalized alkyl substituents at C2 and geminally at C3.For substrates bearing a 2-iodoethyl group at C2 and, at C3, axial vinyl and equatorial cyanomethyl groups, reaction with tri-n-butyltin hydride causes deiodination and the resulting carbon-centered radical adds serially to the vinyl group and thence to the nitrile.A diquinane fused to the pyranoside ring thereby results.If aldehydo and amido groups are used instead of nitrile, the reaction takes a different course.