72733-12-1

Upstream product

• 532-32-1 sodium benzoate 
• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 

Downstream Products

• 42926-89-6 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose 
• 65434-49-3 3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 18685-18-2 3-O-benzyl-1,2:5,6-di-O-isopropylidene-β-L-idofuranose 
• 101475-83-6 3-O-benzyl-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 26597-73-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-ulose 
• 582-52-5 1,2:5,6-diacetone-D-glucose 

Relevant academic research and scientific papers

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.

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.