106445-46-9

Upstream product

• 57783-76-3 benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 100-51-6 benzyl alcohol 
• 102046-36-6 (2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde 
• 530-26-7 D-Mannose 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 77455-30-2 benzyl 6-O-triphenylmethyl-α-D-mannopyranoside 
• 106445-44-7 benzyl 2,3,4-tri-O-benzyl-β-L-glycero-D-manno-heptopyranurononitrile 
• 78561-22-5 benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside 

Downstream Products

• 6946-17-4 L-glycero-D-manno-heptose 
• 106445-50-5 1-((2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-yl)-ethanone 
• 106445-48-1 benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside 

Relevant academic research and scientific papers

NEW SYNTHESES OF D- AND L-GLYCERO-D-MANNO-HEPTOSES

Three methods for the synthesis of the title compounds starting from benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (7) have been elaborated.Conversion of 7 into the cyanohydrin followed by reduction to give the amine and then deamination gave a derivative of L-glycero-D-manno-heptose in low yield.Condensation of 7 with 2-methylfuran gave two stereoisomeric 6-C-(2-methyl-5-furyl) derivatives.The preponderant stereoisomer was ozonised and then reduced to give a derivative of D-glycero-D-manno-heptose.Condensation of 7 with allyloxymethylmagnesium chloride gave derivatives of both heptoses in good yield and with an L-glycero-D-glycero ratio of 3.2:1.Deprotection of these derivatives gave the heptoses in high yield.