p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Base Information

• Chemical Name: p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside
• CAS No.: 140686-52-8
• Molecular Formula: C₂₅H₃₄N₄O₇Si
• Molecular Weight: 530.653
• Mol file: 140686-52-8.mol

Synonyms:p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Chemical Property of p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside

There total 2 articles about p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-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:

benzyl bromide (100-39-0) → p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside (140686-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / sodium hydride / dimethylformamide / 1 h / Ambient temperature

2: 1) aq. 70percent acetic acid, 2) pyridine / 1) 70 deg C, 1.5 h, 2) overnight

With pyridine; sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80050-B

Reference yield:

p-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside (140851-33-8) → p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside (140686-52-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / sodium hydride / dimethylformamide / 1 h / Ambient temperature

2: 1) aq. 70percent acetic acid, 2) pyridine / 1) 70 deg C, 1.5 h, 2) overnight

With pyridine; sodium hydride; acetic acid; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(92)80050-B

Reference yield: 96.0%

ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (99409-32-2) + p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-mannopyranoside (140686-52-8) → p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-mannopyranoside (140686-53-9)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/0008-6215(92)80050-B

upstream raw materials:

benzyl bromide

p-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-mannopyranoside

Downstream raw materials:

p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-mannopyranoside

p-trifluoroacetamidophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-mannopyranosiduronic acid

p-nitrophenyl 4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-azido-3-O-benzyl-2-deoxy-β-D-mannopyranoside

tert-butyl uronate