N-Acetyl-β-D-GlucosaMine 6-Acetate 1,3,4-Tribenzyl Ether

Base Information

• Chemical Name: N-Acetyl-β-D-GlucosaMine 6-Acetate 1,3,4-Tribenzyl Ether
• CAS No.: 129729-33-5
• Molecular Formula: C₃₁H₃₅NO₇
• Molecular Weight: 533.621
• Mol file: 129729-33-5.mol

Synonyms:benzyl 2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of N-Acetyl-β-D-GlucosaMine 6-Acetate 1,3,4-Tribenzyl Ether

Chemical Property:

• Solubility.: Chloroform

Purity/Quality:

N-Acetyl-β-D-Glucosamine6-Acetate1,3,4-TribenzylEther ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: N-Acetyl-β-D-Glucosamine 6-Acetate 1,3,4-Tribenzyl Ether is a derivative of N-Acetyl-D-Glucosamine 6-Acetate (A178205), used in the preparation of the active mutant subtilisin BPN' in DMF via site-directed mutagenesis.

Technology Process of N-Acetyl-β-D-GlucosaMine 6-Acetate 1,3,4-Tribenzyl Ether

There total 1 articles about N-Acetyl-β-D-GlucosaMine 6-Acetate 1,3,4-Tribenzyl Ether 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: 51.0%

Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (4171-69-1) + acetic anhydride (108-24-7) → benzyl 2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (129729-33-5)

Guidance literature:

With sulfuric acid; In acetic acid; at 0 ℃; for 1h;

DOI:10.1016/0008-6215(90)84200-E

Reference yield: 76.0%

benzyl 2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (129729-33-5) → 2-amino-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose hydrochloride (129729-34-6)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 14h; Heating;

DOI:10.1016/0008-6215(90)84200-E

Reference yield:

benzyl 2-acetamido-6-O-acetyl-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (129729-33-5) → 3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose (129729-35-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / 3M hydrochloric acid / tetrahydrofuran / 14 h / Heating

2: 76 percent / M sodium hydroxide / methanol / 2 h / Ambient temperature

With hydrogenchloride; sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1016/0008-6215(90)84200-E

upstream raw materials:

Benzyl 2-N-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

acetic anhydride

Downstream raw materials:

2-amino-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranose hydrochloride

3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose

methyl 6-O-(6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 4-O-(6-O-acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Refernces