benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS No.: 174148-10-8
• Molecular Formula: C₄₈H₅₅NO₁₄
• Molecular Weight: 869.963
• Mol file: 174148-10-8.mol

Synonyms:benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property of benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

There total 1 articles about benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 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: 52.3%

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) + phenyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-D-glucopyranoside → benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (174148-10-8)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/0008-6215(95)00257-X

Reference yield: 93.0%

benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (174148-10-8) → benzyl 3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (174148-11-9)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(95)00257-X

Reference yield:

benzyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (174148-10-8) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1<*>2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1<*>6)-2-O-acetyl-3-O-benzyl-β-D-mannopyranosyl-(1<*>4)-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (174148-15-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / NaOMe / methanol / Ambient temperature

2: 83.5 percent / 4-toluenesulfonic acid / dimethylformamide / Ambient temperature

3: 96.5 percent / acetic anhydride, dimethyl sulfoxide / Ambient temperature

4: 65.7 percent / sodium borohydride / methanol; CH₂Cl₂ / 4 h / Ambient temperature

5: 98 percent / pyridine / Ambient temperature

6: 82 percent / 60percent aq. CH₃COOH / 2 h / 70 °C

7: 1.) Hg(CN)2, molecular sieves 4A / 1.) benzene, nitromethane, reflux, 2.) benzene, nitromethane, 40-45 deg C, overnight

With pyridine; sodium tetrahydroborate; 4 A molecular sieve; sodium methylate; mercury(II) cyanide; acetic anhydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(95)00257-X

upstream raw materials:

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

benzyl 3-O-benzyl-β-D-glucopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl-(1<*>2)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl-(1<*>6)-2-O-acetyl-3-O-benzyl-β-D-mannopyranosyl-(1<*>4)-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

benzyl 2-O-acetyl-3-O-benzyl-β-D-mannopyranosyl-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2R,4aR,6S,8S,8aR)-8-benzyloxy-7-oxo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide