(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate

Base Information

• Chemical Name: (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate
• CAS No.: 230620-35-6
• Molecular Formula: C₆₅H₇₂NO₁₄P
• Molecular Weight: 1122.26
• Mol file: 230620-35-6.mol

Synonyms:(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate

Chemical Property of (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate

There total 12 articles about (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate 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: 69.0%

Phosphorous acid 2-cyano-ethyl ester (2R,3S,4S)-2,3,4-tris-benzyloxy-5-(4-methoxy-benzyloxy)-pentyl ester (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester → (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate (230620-35-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.333333h;

DOI:10.1139/v99-056

Reference yield:

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,55094-38-7,68027-27-0,73111-53-2,128184-63-4,138794-99-7,641635-63-4) → (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate (230620-35-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / i-Pr₂NEt / CH₂Cl₂ / 0.5 h / 20 °C

2: tetrazole / acetonitrile / 1 h

3: 69 percent / MCPBA / CH₂Cl₂ / 0.33 h / 0 °C

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetonitrile; 1: phosphorylation / 2: Condensation / 3: Oxidation;

DOI:10.1139/v99-056

Reference yield:

Methyl 2,3,4-O-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside (67583-56-6) → (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-p-methoxybenzyl-2,3,4-tri-O-benzyl-D-ribityl-5-phosphate (230620-35-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / HBr / acetic acid / 0 °C

2: 83 percent / i-Pr₂NEt / CH₂Cl₂ / 0.5 h / 20 °C

3: tetrazole / acetonitrile / 1 h

4: 69 percent / MCPBA / CH₂Cl₂ / 0.33 h / 0 °C

With 1H-tetrazole; hydrogen bromide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; acetic acid; acetonitrile; 1: deprotection / 2: phosphorylation / 3: Condensation / 4: Oxidation;

DOI:10.1139/v99-056

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

Methyl 2,3,4-O-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside

D-ribose

D-ribose diethyl dithioacetal

Downstream raw materials:

(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-D-ribityl-5-phosphate

(methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-D-ribityl-5-phosphate