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

Base Information

• Chemical Name: 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
• CAS No.: 174148-15-3
• Molecular Formula: C₇₀H₈₆N₂O₂₈
• Molecular Weight: 1403.45

Synonyms: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

Chemical Property of 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

Chemical Property:

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Safty Information:

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Technology Process of 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

There total 9 articles about 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 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:

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → 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 8 steps

1: 52.3 percent / molecular sieves 4A, N-iodosuciinimide, trifluoromethanesulfonic acid / CH₂Cl₂ / 1.5 h / 0 °C

2: 93 percent / NaOMe / methanol / Ambient temperature

3: 83.5 percent / 4-toluenesulfonic acid / dimethylformamide / Ambient temperature

4: 96.5 percent / acetic anhydride, dimethyl sulfoxide / Ambient temperature

5: 65.7 percent / sodium borohydride / methanol; CH₂Cl₂ / 4 h / Ambient temperature

6: 98 percent / pyridine / Ambient temperature

7: 82 percent / 60percent aq. CH₃COOH / 2 h / 70 °C

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

With pyridine; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; 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

Reference yield:

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

1: 83.5 percent / 4-toluenesulfonic acid / dimethylformamide / Ambient temperature

2: 96.5 percent / acetic anhydride, dimethyl sulfoxide / Ambient temperature

3: 65.7 percent / sodium borohydride / methanol; CH₂Cl₂ / 4 h / Ambient temperature

4: 98 percent / pyridine / Ambient temperature

5: 82 percent / 60percent aq. CH₃COOH / 2 h / 70 °C

6: 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; 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

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:

2-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,4,6-tri-O-acetyl-α-D-mannopyranosyl bromide

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

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

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

Downstream raw materials:

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

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