ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside
CAS No.:870074-20-7
Molecular Formula:C₂₆H₃₂N₃O₉PS
Molecular Weight:593.595
Hs Code.:

Synonyms:ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

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Chemical Property of ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

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Technology Process of ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

There total 7 articles about ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-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: 67.0%

: 870074-19-4
ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-1-thio-α-D-mannopyranoside

: 124575-22-0
dibenzyl N,N-diisopropylphosphoroamidate

: 870074-20-7
ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

Guidance literature:: ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-1-thio-α-D-mannopyranoside; dibenzyl N,N-diisopropylphosphoroamidate; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.5h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

: 870074-19-4
ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-1-thio-α-D-mannopyranoside

: 870074-20-7
ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

2: 200 mg / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-tetrazole; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1039/b507898a

Reference yield:

: (2R,3S,4R,5S,6R)-5-Azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-ethylsulfanyl-tetrahydro-pyran-3,4-diol

: 870074-20-7
ethyl 3,4-di-O-acetyl-2-azido-2-deoxy-6-O-dibenzyloxyphosphoryl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 20 °C

2: tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

3: 200 mg / m-CPBA / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-tetrazole; triethylamine tris(hydrogen fluoride); 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b507898a