4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
CAS No.:1157902-57-2
Molecular Formula:C₂₄H₂₆O₇S
Molecular Weight:458.532
Hs Code.:

Synonyms:4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

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Chemical Property of 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

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Technology Process of 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

There total 4 articles about 4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 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: 70.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 108-24-7
acetic anhydride

: 457931-46-3
4-methylphenyl 1-thio-α-D-mannopyranoside

: 1157902-57-2
4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Guidance literature:: benzaldehyde dimethyl acetal; 4-methylphenyl 1-thio-α-D-mannopyranoside; With toluene-4-sulfonic acid; In acetonitrile; at 25 ℃; Inert atmosphere;

acetic anhydride; In acetonitrile; at 50 ℃; Inert atmosphere;
DOI:10.1055/s-0028-1087913

Reference yield:

: 108-24-7
acetic anhydride

: 755002-33-6
para-tolyl (R)-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1157902-57-2
4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h; Molecular sieve; Inert atmosphere;
DOI:10.1039/c3ob40079d

Reference yield:

: 457931-46-3
4-methylphenyl 1-thio-α-D-mannopyranoside

: 1157902-57-2
4-methylphenyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane;
DOI:10.1039/c3ob40079d