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

Base Information

• Chemical Name: Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 123444-64-4
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 123444-64-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl 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: 84.0%

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol (123474-66-8) + benzoic acid (65-85-0,8013-63-6) → Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (123444-64-4)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside (35905-41-0) → Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (123444-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 67 percent / hydrogen / Pd-C / ethanol

2: 92 percent / hydrogen / Pd(OH)2 / ethanol

3: 84 percent / Ph₃P, DIAD / tetrahydrofuran

With di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)80352-X

Reference yield:

methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside (90365-11-0) → Benzoic acid (2R,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester (123444-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / hydrogen / Pd(OH)2 / ethanol

2: 84 percent / Ph₃P, DIAD / tetrahydrofuran

With di-isopropyl azodicarboxylate; hydrogen; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)80352-X

upstream raw materials:

(2R,3S,5R,6S)-2-Hydroxymethyl-6-methoxy-5-methyl-tetrahydro-pyran-3-ol

benzoic acid

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-methylene-α-D-erythro-hexopyranoside

methyl 2,3-dideoxy-4,6-O-benzylidene-2-methyl-α-D-glucopyranoside

Downstream raw materials:

(E)-(3S,7S,8S)-2-Benzenesulfonyl-8,9-bis-benzyloxy-7-benzyloxymethyl-1-[(2S,3S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3,5-dimethyl-non-5-en-1-one

(E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-[(2S,3S,5R,6S)-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-5-methyl-tetrahydro-pyran-2-yl]-3,5-dimethyl-non-5-en-1-one

(E)-(3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-((2S,3S,5R,6S)-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-yl)-3,5-dimethyl-non-5-en-1-one

(2R,3S,5R,6S)-2-((E)-(1S,3S,7S,8S)-8,9-Bis-benzyloxy-7-benzyloxymethyl-1-methoxy-3,5-dimethyl-non-5-enyl)-3,6-dimethoxy-5-methyl-tetrahydro-pyran