(3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one

Base Information

• Chemical Name: (3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one
• CAS No.: 104227-75-0
• Molecular Formula: C₁₃H₁₄N₆O₅
• Molecular Weight: 334.291
• Mol file: 104227-75-0.mol

Synonyms:(3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one

Chemical Property of (3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one

There total 1 articles about (3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one 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: 96.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2S,3S)-2-amino-2-azido-4-hydroxybutanoic acid + 1-(isocyanomethyl)-4-nitrobenzene (92445-49-3) → (3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one (104227-75-0)

Guidance literature:

In methanol; water; for 12h; Ambient temperature;

DOI:10.1039/a700650k

Reference yield: 89.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one (104227-75-0) → 2-[(2S,3S)-3-Azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-azetidin-1-yl]-N-(4-nitro-benzyl)-acetamide (128791-74-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1039/a700650k

Reference yield:

(3S,4S)-3-azido-4-hydroxymethyl-1-(p-nitrobenzylcarbamoylmethyl)azetidin-2-one (104227-75-0) → C19H27N7O6Si

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / imidazole / dimethylformamide / Ambient temperature

2: N₂O₄, NaOAc / CHCl₃ / 1 h / 0 °C

With 1H-imidazole; sodium acetate; dinitrogen tetraoxide; In chloroform; N,N-dimethyl-formamide;

DOI:10.1039/a700650k

upstream raw materials:

formaldehyd

1-(isocyanomethyl)-4-nitrobenzene

Downstream raw materials:

2-[(2S,3S)-3-Azido-2-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-azetidin-1-yl]-N-(4-nitro-benzyl)-acetamide

p-nitrobenzyl (2S,3S)-2-hydroxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate

p-nitrobenzyl (2S,3S)-3-azido-2-(tert-butyldimethylsiloxymethyl)-4-oxoazetidine-1-acetate

p-nitrobenzyl (6S,7S)-3-methoxy-8-oxo-7-phenylacetamido-4-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate