4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

Base Information

• Chemical Name: 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside
• CAS No.: 475101-60-1
• Molecular Formula: C₄₀H₄₄O₁₆
• Molecular Weight: 780.78

Synonyms:4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

Chemical Property of 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

Chemical Property:

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Technology Process of 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

There total 13 articles about 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside 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: 97.0%

4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside (721438-51-3) → 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside (475101-60-1)

Guidance literature:

4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside; With hydrogen; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran;

With iodine; sodium hydrogencarbonate; In tetrahydrofuran;

DOI:10.1016/S0960-894X(02)00327-X

Reference yield:

p-Methoxyphenyl β-D-xylopyranoside (13299-09-7) → 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside (475101-60-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 75 percent / camphorsulfonic acid / dimethylformamide / 5 h / 60 °C

2.1: TMSOTf / CH₂Cl₂ / 1 h / -15 - -10 °C

3.1: 518.1 mg / MeOH; camphorsulfonic acid / CH₂Cl₂ / 2 h

4.1: 77 percent / pyridine / 1.5 h / 20 °C

5.1: H₂ / (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆ / tetrahydrofuran / 2 h

5.2: 95 percent / NaHCO₃; I₂ / tetrahydrofuran; H₂O / 2.5 h / 0 °C

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/07328300701296810

Reference yield:

p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside (13299-05-3) → 4-methoxyphenyl O-(2,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside (475101-60-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 100 percent / Et₃N / methanol; H₂O / 20 °C

2.1: 75 percent / camphorsulfonic acid / dimethylformamide / 5 h / 60 °C

3.1: TMSOTf / CH₂Cl₂ / 1 h / -15 - -10 °C

4.1: 518.1 mg / MeOH; camphorsulfonic acid / CH₂Cl₂ / 2 h

5.1: 77 percent / pyridine / 1.5 h / 20 °C

6.1: H₂ / (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆ / tetrahydrofuran / 2 h

6.2: 95 percent / NaHCO₃; I₂ / tetrahydrofuran; H₂O / 2.5 h / 0 °C

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; hydrogen; triethylamine; (1,5-cyclooctadiene)(MePh₂P)2Ir*PF₆; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1080/07328300701296810

upstream raw materials:

4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

p-Methoxyphenyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside

p-Methoxyphenyl β-D-xylopyranoside

2,4,6-tri-O-acetyl-3-O-allyl-α,β-D-galactopyranose

Downstream raw materials:

4-methoxyphenyl O-(2,4,6-tri-O-acetyl-3-O-allyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

4-methoxyphenyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

4-methoxyphenyl O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-O-(2,4,6-tri-O-acetyl-α-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

4-methoxyphenyl O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3-di-O-(4-methylbenzoyl)-β-D-xylopyranoside

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