(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

Base Information

• Chemical Name: (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
• CAS No.: 230620-37-8
• Molecular Formula: C₇₁H₇₉N₄O₁₇P
• Molecular Weight: 1291.4
• Mol file: 230620-37-8.mol

Synonyms:(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

Chemical Property of (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

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

There total 17 articles about (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 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: 82.0%

2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate (230620-34-5) + (methyl 2,3,4-tri-O-benzyl-β-D-glucopyranosid-6-yl) 2-cyanoethyl 2,3,4-tri-O-benzyl-D-ribityl-5-phosphate (230620-36-7) → (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 (230620-37-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -40 ℃; for 0.5h;

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-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-D-ribityl-5-phosphate (230620-37-8)

Guidance literature:

Multi-step reaction with 5 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

4: 63 percent / DDQ / CH₂Cl₂; H₂O / 4 h

5: 82 percent / TMSOTf / acetonitrile / 0.5 h / -40 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; acetonitrile; 1: phosphorylation / 2: Condensation / 3: Oxidation / 4: deprotection / 5: Condensation;

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-(2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-β-D-galactopyranosyl) 2,3,4-tri-O-benzyl-D-ribityl-5-phosphate (230620-37-8)

Guidance literature:

Multi-step reaction with 6 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

5: 63 percent / DDQ / CH₂Cl₂; H₂O / 4 h

6: 82 percent / TMSOTf / acetonitrile / 0.5 h / -40 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; hydrogen bromide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; acetic acid; acetonitrile; 1: deprotection / 2: phosphorylation / 3: Condensation / 4: Oxidation / 5: deprotection / 6: Condensation;

DOI:10.1139/v99-056

upstream raw materials:

2-azido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-galactopyranosyl trichloroacetimidate

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

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

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

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