phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside
CAS No.:1394857-35-2
Molecular Formula:C₂₈H₂₄Cl₃N₃O₆S
Molecular Weight:636.94
Hs Code.:

Synonyms:phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

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Chemical Property of phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

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Technology Process of phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

There total 9 articles about phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-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: 92.0%

: 1394857-33-0
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside

: 76-02-8
trifluoroacetyl chloride

: 1394857-35-2
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 5h; Inert atmosphere;
DOI:10.1021/jo300722y

Reference yield:

: 108-98-5
thiophenol

: 1394857-35-2
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

2.1: potassium carbonate; water / methanol / 18 h / 60 °C

3.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / methanol / 2.67 h / 20 °C

4.1: toluene-4-sulfonic acid / acetonitrile / 72 h / 20 °C

5.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

5.2: 3 h / 50 °C

6.1: water; acetic acid / 3 h / 100 °C

7.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; water; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo300722y

Reference yield:

: 2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose

: 1394857-35-2
phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridine / dichloromethane / 16 h / 0 - 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

3.1: methanol; sodium / Inert atmosphere

4.1: camphorsulfonic acid / tetrahydrofuran / 2 h / Dean-Stark; Reflux

5.1: potassium hydroxide; water / tetrahydrofuran; methanol / 2 h

6.1: imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate / tetrahydrofuran; methanol / 5 h

7.1: sodium hydride / tetrahydrofuran / 1.5 h / 20 °C

7.2: 3 h / 50 °C

8.1: water; acetic acid / 3 h / 100 °C

9.1: triethylamine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

10.1: triethylamine / dichloromethane / 5 h / 20 °C / Inert atmosphere

With pyridine; methanol; imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; trimethylsilyl trifluoromethanesulfonate; camphorsulfonic acid; water; sodium; sodium hydride; potassium carbonate; acetic acid; triethylamine; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/jo300722y