Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 102804-04-6
• Molecular Formula: C₂₈H₃₂O₈S
• Molecular Weight: 528.623
• Mol file: 102804-04-6.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester

There total 2 articles about Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-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: 78.0%

methyl 4,6-di-O-benzyl-α-D-mannopyranoside (73045-57-5) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (102804-04-6) + Toluene-4-sulfonic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester (102804-03-5) + C35H38O10S2 (102804-07-9)

Guidance literature:

With sodium hydroxide; trimethylbenzylammonium bromide; In benzene; Ambient temperature;

DOI:10.1016/0008-6215(87)80212-4

Reference yield: 21.0%

methyl 4,6-di-O-benzyl-α-D-mannopyranoside (73045-57-5) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (102804-04-6) + Toluene-4-sulfonic acid (2S,3S,4S,5S,6R)-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-pyran-3-yl ester (102804-03-5)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; Ambient temperature;

DOI:10.1016/S0008-6215(00)90642-6

Reference yield:

benzoyl chloride (98-88-4) + Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3-benzyloxy-2-benzyloxymethyl-5-hydroxy-6-methoxy-tetrahydro-pyran-4-yl ester (102804-04-6) → Benzoic acid (2S,3S,4S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester (102804-05-7)

Guidance literature:

DOI:10.1016/S0008-6215(00)90642-6

upstream raw materials:

methyl 4,6-di-O-benzyl-α-D-mannopyranoside

p-toluenesulfonyl chloride

Downstream raw materials:

Benzoic acid (2S,3S,4S,5R,6R)-5-benzyloxy-6-benzyloxymethyl-2-methoxy-4-(toluene-4-sulfonyloxy)-tetrahydro-pyran-3-yl ester