Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 101068-97-7
• Molecular Formula: C₁₆H₂₀O₇
• Molecular Weight: 324.331

Synonyms:Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester

There total 6 articles about Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-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: 91.0%

methyl-4-O-benzoyl-α-L-rhamnopyranoside (69557-83-1) + acetyl chloride (75-36-5) → Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (101068-97-7)

Guidance literature:

With pyridine; In dichloromethane; at -10 - 20 ℃; for 2.5h;

Reference yield: 19.3%

methyl-4-O-benzoyl-α-L-rhamnopyranoside (69557-83-1) + acetyl chloride (75-36-5) → Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (101068-97-7) + Benzoic acid (2S,3S,4R,5R,6R)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (101068-96-6)

Guidance literature:

In pyridine; benzene; 1.) 0 deg C, 20 min, 2.) 20 deg C, 10 min;

DOI:10.1007/BF01142795

Reference yield:

methyl-4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (52681-72-8,71204-48-3,85726-76-7,108319-50-2,145260-87-3) → Benzoic acid (2S,3S,4S,5R,6R)-4-acetoxy-5-hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (101068-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90percent CF₃COOH / CHCl₃ / 0.25 h / 20 °C

2: 40.7 percent / pyridine; benzene / 1.) 0 deg C, 20 min, 2.) 20 deg C, 10 min

With trifluoroacetic acid; In pyridine; chloroform; benzene;

DOI:10.1007/BF01142795

upstream raw materials:

methyl-4-O-benzoyl-α-L-rhamnopyranoside

acetyl chloride

methyl-4-O-benzoyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

benzoyl chloride

Downstream raw materials:

methyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside

methyl 3-O-acetyl-2,4-di-O-benzoyl-α-L-rhamnopyranoside

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