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

Base Information

• Chemical Name: (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribityl-5-phosphate
• CAS No.: 230620-44-7
• Molecular Formula: C₇₁H₇₉N₄O₁₇P
• Molecular Weight: 1291.4
• Mol file: 230620-44-7.mol

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

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

There total 18 articles about (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-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: 84.0%

phosphorous acid 5-(7-azido-8-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,3,4-tris-benzyloxy-pentyl ester 2-cyano-ethyl ester 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-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribityl-5-phosphate (230620-44-7)

Guidance literature:

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

DOI:10.1139/v99-056

Reference yield:

2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol (111549-97-4) → (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribityl-5-phosphate (230620-44-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.33 h / 0 °C

1.2: 89 percent / dimethylformamide / 4 h / 20 °C

2.1: 69 percent / 10 percent Pd/C / methanol; H₂O / 10 h / 60 °C

3.1: 16 percent / TMSOTf / acetonitrile / 0.67 h / -50 °C

4.1: tetrazole / acetonitrile / 0.67 h

5.1: 84 percent / MCPBA / acetonitrile; CH₂Cl₂ / 0.33 h / 0 °C

With 1H-tetrazole; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: Metallation / 1.2: Alkylation / 2.1: deprotection / 3.1: glycosylation / 4.1: glycosylation / 5.1: Oxidation;

DOI:10.1139/v99-056

Reference yield:

5-O-allyl 2,3,4-tri-O-benzyl-D-ribose diethyl dithioacetal (118964-49-1) → (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 1-O-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-L-ribityl-5-phosphate (230620-44-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 86 percent / aq. HgCl₂; CaCO₃ / acetonitrile / 1 h / 20 °C

2.1: 90 percent / NaBH₄ / methanol; H₂O / 10 h

3.1: NaH / dimethylformamide / 0.33 h / 0 °C

3.2: 89 percent / dimethylformamide / 4 h / 20 °C

4.1: 69 percent / 10 percent Pd/C / methanol; H₂O / 10 h / 60 °C

5.1: 16 percent / TMSOTf / acetonitrile / 0.67 h / -50 °C

6.1: tetrazole / acetonitrile / 0.67 h

7.1: 84 percent / MCPBA / acetonitrile; CH₂Cl₂ / 0.33 h / 0 °C

With 1H-tetrazole; sodium tetrahydroborate; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; sodium hydride; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; mercury dichloride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1.1: deprotection / 2.1: Reduction / 3.1: Metallation / 3.2: Alkylation / 4.1: deprotection / 5.1: glycosylation / 6.1: glycosylation / 7.1: 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-L-ribityl-5-phosphate