178458-05-4

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 2622-05-1 allylmagnesium bromide 

Downstream Products

• 270585-44-9 but-2-ynyl 5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-α-D-gluco-non-1-en-4-ulopyranoside 
• 389121-75-9 (Z)-(3R,4S,5R,6R)-2-allylidene-3,4,5-tris(benzyloxy)-6-(benzyloxy)methyltetrahydropyran 
• 389121-76-0 ((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetaldehyde 
• 1000184-72-4 (2R,3R,4S,5R,6R)-2-acetoxy-2-allyl-3,4,5-tris(benzyloxy)-6-(benzyloxy)methyltetrahydropyran 
• 178387-99-0 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-ol 
• 178387-98-9 (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-pyran-2-ol 
• 178388-01-7 2,2-Dimethyl-propionic acid (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-1-benzyloxymethyl-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-oxo-hexyl ester 
• 178388-00-6 2,2-Dimethyl-propionic acid (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-1-benzyloxymethyl-6-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-oxo-hexyl ester 
• 389121-80-6 (E)-4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid ethyl ester 
• 389121-78-2 (E)-5-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-pent-3-en-2-one 
• 389121-77-1 (E)-4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-but-2-enenitrile 
• 389121-79-3 (E)-4-((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-but-2-enal 

Relevant academic research and scientific papers

Facile synthesis of conjugated exo-glycals

Two efficient methods were explored for the synthesis of various conjugated exo-glycals: (i) by nucleophilic addition of sugar lactones with a subsequent dehydration, and (ii) by selenylation of C-glycosides with subsequent selenoxide elimination. These reactions occurred in a stereoselective manner to give exclusively or predominantly the (Z)-isomers of exo-glycals.

Stereochemistry in the synthesis and reaction of exo-glycals.

Two general methods are explored for the stereoselective synthesis of exo-glycals. One method utilizes a nucleophilic addition of fully protected sugar lactones of gluco-, galacto-, and manno-types, followed by the subsequent dehydration, to give the desired exo-glycals with (Z)-configuration. The other method proceeds with selenylation of C-glycosides in a stereoselective manner. The subsequent selenoxide elimination also provides (Z)-exo-glycals. The prepared exo-glycal conjugated esters of either gluco- or manno-type react with allyl alcohol to give exclusively alpha-anomers.