106445-56-1

Upstream product

• 253596-65-5 3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-D-glycero-α-D-manno-heptopyranosid-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose 
• 114894-82-5 benzyl 6-O-tetra-butyldiphenylsilyl-α-D-mannopyranoside 
• 100-39-0 benzyl bromide 
• 1222709-77-4 benzyl 6-O-tetra-butyldiphenylsilyl-2,3,4-O-tribenzyl-α-D-mannopyranoside 
• 1554004-68-0 benzyl 2,3,4-O-tribenzyl-6,7-dideoxy-α-D-hept-6-enopyranoside 
• 100-51-6 benzyl alcohol 
• 78561-22-5 benzyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-α-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 15548-45-5 (2S,3S,4S,5S,6R)-2-benzyloxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol 
• 102046-36-6 (2S,3S,4S,5S,6S)-3,4,5,6-tetrabenzyloxytetrahydropyran-2-carbaldehyde 
• 253596-64-4 3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-α-D-manno-heptopyranosid-6-ulose-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose 
• 858352-14-4 benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid 
• 253596-63-3 (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 57783-76-3 benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 1554004-75-9 benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside 
• 1554004-89-5 benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-L-glycero-α-D-mannoheptopyranoside 
• 1554005-00-3 benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside 
• 732296-48-9 benzyl 7-O-tetra-butyldiphenylsilyl-2,3,4,6-O-tetra-benzyl-L-glycero-α-D-mannoheptopyranoside 
• 582308-13-2 benzyl 2,3,4,6-O-tetrabenzyl-6-deoxy-glycero-α-D-manno-heptopyranoside 
• 1554005-06-9 benzyl 7-O-dibenzyl-phosphono-2,3,4-O-tri-benzyl-6-deoxy-glycero-α-D-mannoheptopyranoside 
• 1554004-98-6 benzyl 7-O-tetra-butyldiphenylsilyl-6-O-(phenorythiocarbonyl)-2,3,4-O-tri-benzyl-D-glycero-α-D-mannoheptopyranoside 
• 1588523-50-5 C₅₈H₅₉NO₁₀Si 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE

An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose (ADP-d, d-heptose) was reported using chemically synthesized d, d-heptose-7-phosphate and the ADP-d, d-heptose biosynthetic enzymes HldE and GmhB M

Convenient approach to higher carbon sugars. First synthesis of the free C12-sugar: D-erythro-L-manno-D-manno-dodecose

The model synthesis of a C12-aldose was initiated from the easily available dimethyl(benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate and 2,3:4,5-di-O-isopropylidene-D-arabinose.

Application of sugar phosphonates for the preparation of higher carbon monosaccharides

Reaction of sugar derived phosphonates [Sug-C(O)CH2P(O)(OMe)2] with sugar aldehydes (Sug'-CHO) provides the higher enones of the general formula Sug-C(O)CH=CH-Sug' with the trans configuration of the double bond. The phosphonate meth

SYNTHESIS OF L-glycero-D-manno-HEPTOSE

The easily accessible benzyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside (2) can be converted, in a highly stereoselective manner, by the two-step Tamao method to benzyl 2,3,4-tri-O-benzyl-β-L-glycero-α-D-manno-heptopyranoside (4a).

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.