phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside
CAS No.:1492048-11-9
Molecular Formula:C₃₀H₃₇N₃O₁₅S
Molecular Weight:711.701
Hs Code.:

Synonyms:phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

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Technology Process of phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

There total 4 articles about phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-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: 47.0%

: 1492048-09-5
2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride

: 108-98-5
thiophenol

: 1492048-11-9
phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In water-d2; ethyl acetate; Inert atmosphere;
DOI:10.1021/ol403140h

Reference yield:

: 1492048-10-8
C₂₄H₃₂N₄O₁₈

: 1492048-11-9
phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: tetraethylammonium chloride / acetonitrile / 6 h / 20 °C / Inert atmosphere

2: tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate / water-d2; ethyl acetate / Inert atmosphere

With tetraethylammonium chloride; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In water-d2; ethyl acetate; acetonitrile;
DOI:10.1021/ol403140h

Reference yield:

: 2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl-(1→4)-1,2,3,6-tetra-O-acetyl-D-mannopyranose

: 1492048-11-9
phenyl-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)-(1→4)-3,6-di-O-acetyl-2-azido-2-deoxy-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogen bromide; acetic acid / 1,2-dichloro-ethane / 2.5 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: ammonium cerium (IV) nitrate; sodium azide / acetonitrile / 12 h / -20 °C / Inert atmosphere

3.1: tetraethylammonium chloride / acetonitrile / 6 h / 20 °C / Inert atmosphere

4.1: tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate / water-d2; ethyl acetate / Inert atmosphere

With sodium azide; ammonium cerium (IV) nitrate; tetraethylammonium chloride; hydrogen bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; acetic acid; In water-d2; ethyl acetate; 1,2-dichloro-ethane; acetonitrile;
DOI:10.1021/ol403140h