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

Base Information

• Chemical Name: Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 51785-62-7
• Molecular Formula: C₁₈H₂₂O₈
• Molecular Weight: 366.368
• Mol file: 51785-62-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-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: 92.0%

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside (2774-22-3,4141-45-1,6748-84-1,6752-75-6,15451-81-7,20750-01-0,35311-30-9,56687-82-2,59121-47-0,72813-11-7,76333-82-9,112968-15-7,130464-34-5) → Benzoic acid (2S,4S,5R,6S)-4,5-diacetoxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester (51785-64-9) + Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (51785-62-7)

Guidance literature:

With di-tert-butyl peroxide; triisopropylsilanethiol; In octane; chlorobenzene; for 2h; Further Variations:; Reagents; Product distribution; Heating;

DOI:10.1039/b212303g

Reference yield: 85.0%

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside (2774-22-3,4141-45-1,6748-84-1,6752-75-6,15451-81-7,20750-01-0,35311-30-9,56687-82-2,59121-47-0,72813-11-7,76333-82-9,112968-15-7,130464-34-5) → Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (51785-62-7)

Guidance literature:

With 2,3,5-trimethyl-pyridine; 2,2-bis(tert-butylperoxy)butane; 2,3,3,4,4,5-hexamethyl-2-hexanethiol; In octane; chlorobenzene; for 3h; Heating;

DOI:10.1016/S0040-4039(00)01904-3

Reference yield: 82.0%

Acetic acid (2S,4aR,6S,7R,8S,8aR)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (553663-03-9) → Benzoic acid (2R,3R,4S,5R,6S)-4,5-diacetoxy-6-methoxy-2-methyl-tetrahydro-pyran-3-yl ester (51785-62-7)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Heating;

DOI:10.1021/ol034741r

upstream raw materials:

acetic anhydride

methyl 4-O-benzoyl-6-deoxy-α-D-glucopyranoside

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyraniside

Acetic acid (2S,4aR,6S,7R,8S,8aR)-7-acetoxy-2-[2-(2-iodo-phenyl)-ethylsulfanylcarbonyl]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester