tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside
CAS No.:502692-38-8
Molecular Formula:C₂₅H₂₈Cl₃NO₇S
Molecular Weight:592.925
Hs Code.:

Synonyms:tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

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Chemical Property of tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

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Technology Process of tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

There total 4 articles about tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside 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: 90.0%

: 502692-37-7
Acetic acid (2R,4aR,6S,7R,8R,8aS)-2-phenyl-6-p-tolylsulfanyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

: 502692-38-8
tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

Guidance literature:: With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo0206420

Reference yield:

: 323195-45-5
p-methylphenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside

: 502692-38-8
tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: (+/-)-10-camphorsulfonic acid / acetonitrile / 2 h / 20 °C

2: 1.17 g / DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

3: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

With pyridine; triethylsilane; dmap; camphor-10-sulfonic acid; trifluoroacetic acid; In dichloromethane; acetonitrile;
DOI:10.1021/jo0206420

Reference yield:

: 220645-20-5
p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside

: 502692-38-8
tolyl 3-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroethoxycarbonylamino-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: NaOMe; MeOH / CH₂Cl₂ / 2 h / 0 °C

2: (+/-)-10-camphorsulfonic acid / acetonitrile / 2 h / 20 °C

3: 1.17 g / DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

4: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

With pyridine; methanol; triethylsilane; dmap; camphor-10-sulfonic acid; sodium methylate; trifluoroacetic acid; In dichloromethane; acetonitrile; 1: Zemplen deacetylation;
DOI:10.1021/jo0206420