103516-28-5

Upstream product

• 532-32-1 sodium benzoate 
• 103516-27-4 (2R,3R,4R,5S)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-bis<(methylsulfonyl)oxy>ethyl>-4-methyl-4-vinyltetrahydrofuran 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 103516-19-4 (2R,3R,4R,5S)-4-(formylmethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran 
• 57466-98-5 (Z)-ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6(3aH,5H,6aH)-ylidene)acetate 
• 57466-95-2 (E)-ethyl 2-((3aR,5S,6aR)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethylfuro[2,3-d][1,3]dioxol-6(3aH,5H,6aH)-ylidene)acetate 
• 103516-13-8 2-[(3aR,5S,6aR)-5-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-dihydro-furo[2,3-d][1,3]dioxol-(6E)-ylidene]-ethanol 
• 103516-15-0 (2R,3R,4R,5S)-4-<(ethoxycarbonyl)methyl>-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran 
• 103537-73-1 (2R,3R,4R,5S)-4-(2-hydroxyethyl)-2,3-(isopropylidenedioxy)-5-<(1R)-1,2-(isopropylidenedioxy)ethyl>-4-vinyltetrahydrofuran 
• 103516-24-1 (2R,3R,4R,5S)-5-<(1R)-1,2-dihydroxyethyl>-2,3-(isopropylidenedioxy)-4-methyl-4-vinyltetrahydrofuran 
• 103516-12-7 (Z)-3-deoxy-3-C-[(hydroxymethyl)methylene]-1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose 
• 103516-20-7 3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-methyl-3-C-vinyl-α-D-allofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 57466-95-2 (E)-3-deoxy-3-C-<(ethoxycarbonyl)methylene>-1,2:5,6-di-o-isopropylidene-α-D-ribo-hexofuranose 

Relevant academic research and scientific papers

INTRODUCTION OF gem-DIALKYL GROUP TO HEXOFURANOSE BY ORTHO ESTER CLAISEN REARRANGEMENT

The ortho ester Claisen rearrangement of D-ribo- or L-lyxo-hexofuranose derivative which possesses an allyl alcohol functionality on C-3, proceeds stereoselectively to give a 3-C-dialkylated product.The stereochemistry of a newly introduced quaternary center of the product was unambiguously established by a chemical modification.

Ortho Ester Claisen Rearrangements of Three 3-C-(Hydroxymethyl)methylene Derivatives of Hexofuranose: Stereoselective Introduction of a Quaternary Center on C-3 of D-ribo-, L-lyxo-, and D-arabino-Hexofuranoses

Ortho ester Claisen rearrangements of (E)-3-deoxy-3-C--1,2:5,6-di-O-isopropylidene-α-D-ribo-hexofuranose (3-E), -β-L-lyxo-hexafuranose (12-E), and -β-D-arabino-hexofuranose (33-E) proceeded with high stereoselectivity to provide the rearranged products 13, 15, and 34, respectively, in acceptable yields.The rearrangements of the corresponding Z isomers 3-Z, 12-Z, and 33-Z were also investigated.The stereochemistries of the newly introduced quaternary center on C-3 of compounds 13, 15, and 34 were established unambiguouosly by chemical modifications of each rearranged product.