220172-74-7

Upstream product

• 55610-71-4 methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 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 
• 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 
• 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] 
• 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 
• 220172-58-7 (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 
• 220172-55-4 dimethyl (methyl 2,3,4-tri-O-benzyl-D-gluco-heptopyranos-6-ulos-7-yl)phosphonate 
• 120403-24-9 (methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosiduronyl)-(triphenylphosphoranylidene)methane 
• 100-39-0 benzyl bromide 

Downstream Products

• 220172-76-9 (2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-((1R,2R,3S,4S,5R,6R)-1,2,3,4,5,6,7-heptakis-benzyloxy-heptyl)-6-methoxy-tetrahydro-pyran 

Relevant academic research and scientific papers

Approach to higher carbon sugars functionalized at both terminal positions

Model study on the synthesis of higher carbon sugars using the phosphonate approach is presented. A C7 sugar phosphonate was reacted with a C5 sugar aldehyde under mild phase-transfer conditions to afford the C12-α,β-unsaturated ketone. Proper functionalization of the internal C3-carbon bridge provided derivative suitable for differentiation at both 'ends', thus allowing to introduce the desired functionality either at the C-1 or C-12 positions.

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.