(2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol

Base Information

• Chemical Name: (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol
• CAS No.: 112330-08-2
• Molecular Formula: C₃₃H₄₀O₈
• Molecular Weight: 564.676

Synonyms:(2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol

Chemical Property of (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol

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Technology Process of (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol

There total 4 articles about (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol (22323-82-6,36543-79-0) + 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose (74372-90-0,112289-38-0,135202-48-1,148888-66-8,71696-32-7) → (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol (112330-08-2)

Guidance literature:

With bis(4-fluorophenyl)(hydroxy)borane; In acetonitrile; at 0 ℃; for 2h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00926

Reference yield: 62.0%

3,4,6-tri-O-benzyl-D-mannopyranose (20672-66-6) + [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate (76679-39-5) → (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol (112330-08-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1.) 15 min, 2.) 24 h;

Reference yield: 53.0%

3,4,6-tri-O-benzyl-D-mannopyranose (20672-66-6) + [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate (76679-39-5) → (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-β-D-mannopyranosyl)glycerol (112330-08-2) + (2S)-1,2-O-isopropylidene-3-O-(3',4',6'-tri-O-benzyl-α-D-mannopyranosyl)glycerol (112330-09-3) + 2,3-O-Isopropylidene-1-O-(3,4,6-tri-O-benzyl-2-O-(2,2-dimethyl-1,3-dioxolan-4R-yl)-β-D-mannopyranosyl)-D-glycerol

Guidance literature:

With sodium hydride; In acetonitrile; 1.) 15 min, 2.) 11 h;

upstream raw materials:

(2S)-1-O-<(3'R,4'R,5'R)-5'-hydroxy-3',4',6'-tribenzyloxyhex-1'(Z)-enyl>-2,3-O-isopropylideneglycerol

3,4,6-tri-O-benzyl-D-mannopyranose

[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate

(S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol

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