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

Base Information

• Chemical Name: Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 79386-70-2
• Molecular Formula: C₁₅H₁₉BrO₅
• Molecular Weight: 359.217

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

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

Chemical Property:

Purity/Quality:

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

There total 2 articles about Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-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: 88.0%

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside (84170-91-2) → Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester (79386-70-2)

Guidance literature:

With N-Bromosuccinimide; In tetrachloromethane; Heating;

DOI:10.1016/S0040-4039(00)86735-0

Reference yield:

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside (3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2,2880-96-8) → Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester (79386-70-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / tetrahydrofuran; diethyl ether / 168 h / 80 °C

2: 85 percent / NBS; BaCO₃ / CCl₄ / 0.58 h / Heating

With N-Bromosuccinimide; barium carbonate; In tetrahydrofuran; tetrachloromethane; diethyl ether;

DOI:10.1016/S0960-894X(02)00722-9

Reference yield: 97.0%

Benzoic acid (2S,3S,4S,5S,6S)-2-bromomethyl-5-hydroxy-6-methoxy-4-methyl-tetrahydro-pyran-3-yl ester (79386-70-2) → Benzoic acid (2R,3S,4S,5S,6S)-5-hydroxy-6-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl ester (82793-06-4)

Guidance literature:

With hydrogen; triethylamine; Ra-Ni;

DOI:10.1016/S0040-4039(00)86735-0

upstream raw materials:

methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-α-D-altropyranoside

methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside

Downstream raw materials:

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

Benzoic acid (1R,2S,3S)-3,4-dihydroxy-2-methyl-1-vinyl-butyl ester

Benzoic acid (R)-1-((R)-(S)-1-oxiranyl-ethyl)-allyl ester

Benzoic acid (1R,2S,3R)-3-hydroxy-2-methyl-6-trimethylsilanyl-1-vinyl-hex-5-ynyl ester

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