4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester
• CAS No.: 122926-92-5
• Molecular Formula: C₃₃H₄₂O₁₉
• Molecular Weight: 742.685

Synonyms:4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

Chemical Property of 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

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Technology Process of 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester

There total 5 articles about 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester 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%

Methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside (87591-35-3) + 3,4,6-Tri-O-acetyl-1,2-O-<(1-cyano)-4-methoxybenzylidene>-α-D-galactopyranose (123000-84-0) → 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (122926-92-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1016/0008-6215(93)80006-Z

Reference yield:

4-methoxy-benzoyl chloride (100-07-2) → 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (122926-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / pyridine / acetonitrile / Ambient temperature

2: Ac₂O, AcBr, AcOH, H₂O / CHCl₃ / 2 h / 20 °C

3: 71 percent / Bu₄NBr / acetonitrile / 12 h / 20 °C

4: 97 percent / triphenylmethylium perchlorate / CH₂Cl₂ / 17 h / 20 °C

With pyridine; Acetyl bromide; tetrabutylammomium bromide; water; triphenylmethyl perchlorate; acetic anhydride; acetic acid; In dichloromethane; chloroform; acetonitrile;

DOI:10.1016/0008-6215(93)80006-Z

Reference yield:

3,4,6-Tri-O-acetyl-2-O-(p-methoxybenzoyl)-α-D-galactopyranosyl bromide (117991-72-7) → 4-Methoxy-benzoic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl ester (122926-92-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / Bu₄NBr / acetonitrile / 12 h / 20 °C

2: 97 percent / triphenylmethylium perchlorate / CH₂Cl₂ / 17 h / 20 °C

With tetrabutylammomium bromide; triphenylmethyl perchlorate; In dichloromethane; acetonitrile;

DOI:10.1016/0008-6215(93)80006-Z

upstream raw materials:

Methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside

3,4,6-Tri-O-acetyl-1,2-O-<(1-cyano)-4-methoxybenzylidene>-α-D-galactopyranose

4-methoxy-benzoyl chloride

3,4,6-Tri-O-acetyl-2-O-(p-methoxybenzoyl)-α-D-galactopyranosyl bromide

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