(2S,3S)-3α-Amino-2α-carbamoyloxymethyl-4-oxo-1-azetidinesulfonic acid

Base Information

• Chemical Name: (2S,3S)-3α-Amino-2α-carbamoyloxymethyl-4-oxo-1-azetidinesulfonic acid
• CAS No.: 88852-06-6
• Molecular Formula: C₅H₉N₃O₆S
• Molecular Weight: 239.209
• Mol file: 88852-06-6.mol

Synonyms:(2S,3S)-3α-Amino-2α-carbamoyloxymethyl-4-oxo-1-azetidinesulfonic acid

Chemical Property of (2S,3S)-3α-Amino-2α-carbamoyloxymethyl-4-oxo-1-azetidinesulfonic acid

Chemical Property:

• PSA: 161.40000
• LogP: -0.15810

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S,3S)-3α-Amino-2α-carbamoyloxymethyl-4-oxo-1-azetidinesulfonic acid

There total 2 articles about (2S,3S)-3α-Amino-2α-carbamoyloxymethyl-4-oxo-1-azetidinesulfonic acid 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: 95.0%

sodium (3S,4S)-3-(benzyloxycarboxamido)-4-<(carbamoyloxy)methyl>-2-oxoazetidine-1-sulfonate (86299-42-5) → (3S,4S)-3-amino-4-[(carbamoyloxy)methyl]-2-oxo-azetidine-1-sulfonic acid (88852-06-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; water; for 1h; under 760 Torr;

DOI:10.1021/jo00219a009

Reference yield:

isocyanatophosphonic dichloride (870-30-4) + tetrabutylammonium (3S,4S)-3-<(benzyloxycarbonyl)amino>-4-(hydroxymethyl)-2-oxoazetidine-1-sulfonate (92973-33-6,115935-89-2) → (3S,4S)-3-amino-4-[(carbamoyloxy)methyl]-2-oxo-azetidine-1-sulfonic acid (88852-06-6)

Guidance literature:

With hydrogen; potassium hydrogencarbonate; palladium on activated charcoal; Multistep reaction; 1.) dichloroethane, -20 - (-15) deg C, 2h; 2.) EtOH, 1.5 h. r.t., water;

DOI:10.1248/cpb.33.3798

Reference yield:

2-(2-amino-4-thiazolyl)-2-[[(Z)-(p-nitrobenzyloxycarbonyl)-methoxy]-imino]acetic acid-2-benzothiazolyl-thioester + (3S,4S)-3-amino-4-[(carbamoyloxy)methyl]-2-oxo-azetidine-1-sulfonic acid (88852-06-6) → (3S,4S)-3-[(Z)-2-(2-amino-4-thiazolyl)-2-[[(p-nitrobenzyloxycarbonyl)methoxy]imino]acetamido]-4-carbamoyloxymethyl-2-oxo-1-azetidinesulphonic acid sodium salt

Guidance literature:

upstream raw materials:

isocyanatophosphonic dichloride

tetrabutylammonium (3S,4S)-3-<(benzyloxycarbonyl)amino>-4-(hydroxymethyl)-2-oxoazetidine-1-sulfonate

sodium (3S,4S)-3-(benzyloxycarboxamido)-4-<(carbamoyloxy)methyl>-2-oxoazetidine-1-sulfonate

Downstream raw materials:

Carumonam

Refernces

• 1、 Wei,De Bernardo,Tengi,et al.. "Synthesis of chiral β-lactams using L-ascorbic acid". . p. 3462 - 3467. Retrieved 2007/10/02.