phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

Base Information

Chemical Name:phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside
CAS No.:1227612-69-2
Molecular Formula:C₃₅H₃₉N₃O₄SSi
Molecular Weight:625.864
Hs Code.:

Synonyms:phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

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Chemical Property of phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

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Technology Process of phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

There total 5 articles about phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside 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: 94.0%

: 1356031-04-3
phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-galactopyranoside

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1227612-69-2
phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; regioselective reaction;
DOI:10.1016/j.tet.2011.11.088

Reference yield:

: 1356031-02-1
phenyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-galactopyranoside

: 1227612-69-2
phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: methanol; (R)-10-camphorsulfonic acid / dichloromethane / 24 h

2: 1H-imidazole / N,N-dimethyl-formamide / 2 h

With 1H-imidazole; methanol; (R)-10-camphorsulfonic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.11.088

Reference yield:

: 197663-12-0
phenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-1-thiol-D-galactopyranoside

: 1227612-69-2
phenyl 2-azido-3-O-benzyl-6-O-tert-butyl-diphenylsilyl-2-deoxy-1-thio-α-D-galactopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium methylate / methanol / 1 h

1.2: IR₁₂₀ H⁺

2.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 40 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

3.2: 3 h

4.1: methanol; (R)-10-camphorsulfonic acid / dichloromethane / 24 h

5.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h

With 1H-imidazole; methanol; (R)-10-camphorsulfonic acid; sodium methylate; sodium hydride; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2011.11.088