2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime

Base Information

• Chemical Name: 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime
• CAS No.: 140183-54-6
• Molecular Formula: C₂₀H₂₆N₂O₁₀
• Molecular Weight: 454.434
• Mol file: 140183-54-6.mol

Synonyms:2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime

Chemical Property of 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime

There total 8 articles about 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime 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: 78.0%

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose (99194-76-0,140183-53-5) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime (140183-54-6)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; In methanol; for 2h; Heating;

Reference yield: 74.0%

3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose (99194-76-0,140183-53-5) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime (140183-54-6)

Guidance literature:

With pyridine; hydroxylamine hydrochloride; In methanol;

DOI:10.1016/S0040-4039(00)77717-3

Reference yield:

2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate (35946-66-8) → 2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucose oxime (140183-54-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / (NH₄)2CO₃ / methanol; tetrahydrofuran

2: 74 percent / NH₂OH*HCl, pyridine / methanol

With pyridine; hydroxylamine hydrochloride; ammonium carbonate; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)77717-3

upstream raw materials:

3,4,6-tri-O-acetyl-2-{[(benzyloxy)carbonyl]amino}-2-deoxy-β-D-glucopyranose

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-imidazol-1-ylthiocarbonyloxy-D-glucononitrile

Acetic acid (1R,2R,3S,4R,5S)-2-acetoxy-3-acetoxymethyl-4-benzyloxyamino-5-benzyloxycarbonylamino-cyclopentyl ester

Acetic acid (1R,2R,3R,5S)-2-acetoxy-3-acetoxymethyl-4-benzyloxyamino-5-benzyloxycarbonylamino-cyclopentyl ester

2-benzyloxycarbonylamino-2-deoxy-3,4,6-tri-O-acetyl-5-phenoxy(thiocarbonyl)oxy-D-glucose O-benzyl oxime