2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

Base Information

• Chemical Name: 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine
• CAS No.: 192188-32-2
• Molecular Formula: C₂₂H₂₆N₂O₁₃
• Molecular Weight: 526.454
• Mol file: 192188-32-2.mol

Synonyms:2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

Chemical Property of 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine

There total 3 articles about 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine 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:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (192188-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe, Et₃N / methanol

2: pyridine / 16 h

With pyridine; sodium methylate; triethylamine; In methanol;

DOI:10.1039/a700549k

Reference yield:

4-nitrobenzyl chloroformate (4457-32-3) → 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (192188-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe, Et₃N / methanol

2: pyridine / 16 h

With pyridine; sodium methylate; triethylamine; In methanol;

DOI:10.1039/a700549k

Reference yield:

acetic anhydride (108-24-7) + ((3R,4R,5S,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 4-nitro-benzyl ester → 2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (192188-32-2)

Guidance literature:

With pyridine; for 16h; Yield given;

DOI:10.1039/a700549k

upstream raw materials:

acetic anhydride

(+)-D-glucosamine hydrochloride

4-nitrobenzyl chloroformate

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-((2R,3R,4S,5R,6R)-4,5,6-tris-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl]-carbamic acid 4-nitro-benzyl ester

[(2R,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yl]-carbamic acid 4-nitro-benzyl ester