115935-89-2

Usage

Uses

Used in Organic Synthesis:
(3R,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt is used as a chiral building block for the preparation of pharmaceuticals and agrochemicals. Its unique structural and chemical properties make it a valuable component in the synthesis of enantiomerically pure compounds.
Used in Chemical Reactions:
(3R,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt is used as a catalyst or reagent in various chemical reactions. Its chiral nature and functional groups can facilitate specific transformations and improve the efficiency of certain processes.
Further research and development of (3R,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt may lead to new applications and potential benefits in the field of organic chemistry.

Upstream product

• 92754-75-1 (2S,3R)-2-<(benzyloxycarbonyl)amino>-3-hydroxy-4-butanolide 
• 92973-27-8 2-benzyloxycarbonylamino-4-O-chloroacetyl-2-deoxy-3-O-mesyl-D-threonamide 
• 115764-14-2 2-benzyloxycarbonylamino-4-O-chloroacetyl-2-deoxy-D-threonamide 
• 92973-31-4 2-benzyloxycarbonylamino-4-O-chloroacetyl-2-deoxy-3-O-mesyl-D-threonamide-N-sulphonic acid tetrabutylammonium salt 
• 104406-47-5 erythro-Cbz-HyAsp(OMe)-OH 
• 92973-23-4 (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-hydroxybutanamide 
• 92973-44-9 2-<(benzyloxycarbonyl)amino>-2-deoxy-3,4-O-isopropylidene-L-erythronamide 
• 92754-76-2 (2S,3R)-2-<(benzyloxycarbonyl)amino>-3,4-dihydroxybutanamide 
• 97764-69-7 (2S,3R)-2-<(benzyloxycarbonyl)amino>-4-(chloroacetoxy)-3-(mesyloxy)butanamide 
• 97764-71-1 C₁₆H₃₆N⁽¹⁺⁾*C₁₅H₁₈ClN₂O₁₁S₂^(1-) 

Downstream Products

• 97781-99-2 (2S,3S)-3-Benzyloxycarbonylamino-2-(2-chloro-acetylcarbamoyloxymethyl)-4-oxo-azetidine-1-sulfonatetetrabutyl-ammonium; 
• 115887-90-6 (3S,4R)-3-benzyloxycarbonylamino-4-mesyloxymethyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 115764-26-6 (3S,4R)-3-benzyloxycarbonylamino-4-mesyloxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt 
• 115935-91-6 (3S,4R)-3-benzyloxycarbonylamino-4-carbamoyloxymethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt 
• 115887-89-3 (3S,4R)-3-benzyloxycarbonylamino-4-iodomethyl-2-oxoazetidine-1-sulphonic acid tetrabutylammonium salt 
• 115935-92-7 (3S,4R)-3-benzyloxycarbonylamino-4-carbamoyloxymethyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 115935-93-8 (3S,4R)-3-benzyloxycarbonylamino-4-iodomethyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 115887-91-7 (3S,4R)-3-benzyloxycarbonylamino-4-methyl-2-oxoazetidine-1-sulphonic acid sodium salt 
• 80082-62-8 (3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid,tetrabutylammonium salt 
• 115764-24-4 (3S,4R)-3-benzyloxycarbonylamino-2-oxo-4-phenoxy-carbonyloxymethylazetidine-1-sulphonic acid tetrabutylammonium salt 
• 115887-86-0 (3S,4R)-3-benzyloxycarbonylamino-2-oxo-4-phenoxy-carbonyloxymethylazetidine-1-sulphonic acid sodium salt 
• 113599-60-3 (3S,4S)-3-(benzyloxycarboxamido)-4-<<(tert-butyldimethylsilyl)oxy>methyl>-2-azetidinone 
• 1393717-48-0 C₁₆H₃₆N⁽¹⁺⁾*C₁₈H₂₇N₂O₇SSi^(1-) 
• 86299-42-5 sodium (3S,4S)-3-(benzyloxycarboxamido)-4-<(carbamoyloxy)methyl>-2-oxoazetidine-1-sulfonate 

Relevant academic research and scientific papers

Enantioselective Synthesis of (3S)-trans-4-(Substituted Methyl)monobactams from 2,3-O-Isopropylidene-D-glyceraldehyde

The enantioselective synthesis of various (3S)-trans-4-(substituted methyl)-2-oxoazetidine-1-sulphonic acid derivatives from 2,3-O-isopropylidene-D-glyceraldehyde is described.Reaction of this aldehyde with trimethylsilyl cyanide gave a 80:20 ratio of the corresponding threo and erythro α-amino-nitriles, which by amino protection and subsequent treatment with basic hydrogen peroxide provided the corresponding α-amino carboxamides.Successive selective protection, activation, sulphonation and, finally, stereospecific cyclization of the threo α-carboxamide yielded (2S,4R)-3-benzyloxycarbonylamino-4-hydroxymethyl-2-oxoazetidine-1-sulphonic acid, an intermediate for the synthesis of the corresponding 4-acyloxymethyl-, 4-carbamoyloxymethyl-, 4-methylsulphonyloxy-methyl-, 4-iodomethyl-, and 4-methyl-2-oxozetidines.

A Novel Synthesis of the Monobactam Antibiotic Carumonam

A novel synthesis of the monobactam 4, a precursor of the antibiotic carumonam (3), has been achieved via the epoxide methyl (2R,3S)-4-acetoxy-2,3-epoxybutyrate (10).The latter was prepared from calcium L-threonate in three steps and 85percent overall yield.In a related study, ethyl (2R,3S)-4-hydroxy-2,3-epoxybutyrate (17) was prepared from L-(+)-tartaric acid in 45percent overall yield.Treatment of the sodium salt derived from 10 or 17 with ammonia led to a stereo- and regiospecific opening of the oxirane ring to give 20, after esterification, amide formation, and protection of the amino group.Conversion of 20 into 4 was accomplished by selective protection of the primary hydroxy group with chloroacetyl chloride, mesylation, sulfonation with 2-picoline-SO3, and ring closure with potassium bicarbonate.