methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 1281971-16-1
• Molecular Formula: C₃₅H₄₃NO₈
• Molecular Weight: 605.728
• Mol file: 1281971-16-1.mol

Synonyms:methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 5 articles about methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-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: 93.0%

methyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (10583-67-2,117153-62-5,10583-66-1) + di-tert-butyl dicarbonate (24424-99-5) → methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (1281971-16-1)

Guidance literature:

With dmap; In tetrahydrofuran; for 42h; Reflux;

DOI:10.1002/ejoc.201200522

Reference yield:

benzyl bromide (100-39-0) → methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (1281971-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 16 h / 0 °C

2: dmap / tetrahydrofuran / 16 h / Reflux

With dmap; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/c2ob26105g

Reference yield:

methyl N-acetyl-D-glucosamine (3055-46-7,3946-01-8,5627-24-7,6082-04-8,6082-22-0,17327-09-2,22256-76-4,32087-35-7,32087-36-8,95341-97-2,114029-61-7,114612-10-1,114612-13-4,116559-74-1) → methyl 2-[N-acetyl-N-(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (1281971-16-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

2: dmap / tetrahydrofuran / 6 h / Reflux

With dmap; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo1023156

upstream raw materials:

methyl N-acetyl-D-glucosamine

methyl 2-(N-acetylamino)-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

di-tert-butyl dicarbonate

N-Acetyl-D-glucosamine

Downstream raw materials:

methyl 2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-[(tert-butoxycarbonyl)amino]-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl 2-methylamino-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranoside

methyl 2-N-methyl-(2-benzyloxy)acetamido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranoside