p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside
• CAS No.: 1541179-34-3
• Molecular Formula: C₆₃H₆₄O₁₄
• Molecular Weight: 1045.19

Synonyms:p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside

Chemical Property of p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside

There total 5 articles about p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-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:

O-(3-O-acetyl-2,4,6-tri-O-benzyl-D-glucopyranosyl) N-phenyltrifluoroacetimidate + C34H34O8 (1541178-94-2) → p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside (1541179-32-1) + p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside (1541179-34-3)

Guidance literature:

With methyl trifluoromethanesulfonate; In dichloromethane; at -35 - -15 ℃; for 0.583333h; Overall yield = 94 %; Molecular sieve;

DOI:10.1016/j.carres.2013.11.016

Reference yield:

4-methoxyphenyl 4,6-di-O-benzylidene-β-D-glucopyranoside → p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside (1541179-32-1) + p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside (1541179-34-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: di(n-butyl)tin oxide / toluene / 6 h / Reflux

1.2: 80 - 90 °C

2.1: pyridine; dmap

3.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 20 °C / Inert atmosphere

4.1: methyl trifluoromethanesulfonate / dichloromethane / 0.58 h / -35 - -15 °C / Molecular sieve

With pyridine; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; di(n-butyl)tin oxide; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.carres.2013.11.016

Reference yield:

p-methoxyphenyl 4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside (1418284-22-6) → p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside (1541179-32-1) + p-methoxyphenyl 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-glucopyranosyl-(1→6)-3-O-benzoyl-2,4-di-O-benzyl-β-D-glucopyranoside (1541179-34-3)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine; dmap

2: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 20 °C / Inert atmosphere

3: methyl trifluoromethanesulfonate / dichloromethane / 0.58 h / -35 - -15 °C / Molecular sieve

With pyridine; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2013.11.016

upstream raw materials:

p-methoxyphenyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

C₃₄H₃₄O₈

p-methoxyphenyl 4,6-O-benzylidene-2-O-benzyl-β-D-glucopyranoside

benzoyl chloride

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