phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

Base Information

• Chemical Name: phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside
• CAS No.: 930576-68-4
• Molecular Formula: C₁₉H₂₁N₃O₄S
• Molecular Weight: 387.459
• Mol file: 930576-68-4.mol

Synonyms:phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

Chemical Property of phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside

There total 7 articles about phenyl 2-azido-3-O-benzyl-2-deoxy-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: 97.0%

phenyl 4,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside (928260-34-8) → phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside (930576-68-4)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1021/jo101779v

Reference yield:

7-azido-8-benzyloxy-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine → phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside (930576-68-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 1h; Heating;

DOI:10.1002/ejoc.200600759

Reference yield:

7-azido-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol → phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranoside (930576-68-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / dimethylformamide / 0 °C

2: p-toluenesulfonic acid hydrate / methanol / 1 h / Heating

With sodium hydride; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600759

upstream raw materials:

phenyl 2-azido-2-deoxy-1-thio-α-D-mannopyranoside

phenyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-mannopyranoside

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

1,4,6-tri-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α/β-D-mannopyranoside

Downstream raw materials:

phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-α-D-mannopyranosiduronic acid

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

3-O-(6-O-methyl-6-oxy-4-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranosyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

C₁₇H₁₈⁽²⁾H₃N₃O₇