220172-76-9

Upstream product

• 100-39-0 benzyl bromide 
• 220172-74-7 (2R,3R,4S,5S,6R,7R)-5,6,7-Tris-benzyloxy-7-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-heptane-1,2,3,4-tetraol 
• 55610-71-4 methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 
• 120403-24-9 (methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosiduronyl)-(triphenylphosphoranylidene)methane 
• 220172-55-4 dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate 
• 220172-58-7 (E)-(R)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol 
• 220172-57-6 (E)-3-((4S,5R,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-1-((2S,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenone 
• 220172-59-8 (4S,5R,4'R)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl] 
• 1054655-44-5 methyl 2,3,4,6,7,8-hexa-O-benzyl-9,10:11,12-di-O-isopropylidene-α-L-erythro-L-manno-D-gluco-1,5-pyranoside 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 220172-60-1 (1R,2R,3R)-3-Benzyloxy-1-((4R,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propane-1,2-diol 

Relevant academic research and scientific papers

Phosphonate versus phosphorane method in the synthesis of higher carbon sugars. Preparation of D-erythro-L-manno-D-glucododecitol

Higher sugar (C12 and C13) dialdose precursors 5, 10 and 15 were obtained by a coupling of C7-phosphorane 1 or C7-phosphonates 2 and 13 with C5- or C6-sugar aldehydes. These compounds were converted into higher dialdoses by (i) stereoselective reduction of a carbonyl group with zinc borohydride followed by (ii) osmylation of the resulting allylic alcohols. One of these derivatives - compound 8a - was converted into D-erythro-L-manno-D-gluco-dodecitol 23 on a 0.5 g scale.