220172-62-3

Upstream product

• 4933-77-1 (3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde 
• 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 
• 55610-71-4 methyl (methyl-2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate 

Downstream Products

• 220172-63-4 (E)-(R)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-en-1-ol 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 103597-20-2 methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 220172-91-8 (3aR,5R,5aS,8aS,8bR)-5-[(E)-(R)-3-Benzyloxy-3-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-propenyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 
• 220172-94-1 (1R,2R,3R)-3-Benzyloxy-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-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.