140645-28-9

Basic information

• Product Name: ((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE
• Synonyms: ((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE
• CAS NO: 140645-28-9
• Molecular Formula: C₁₈H₂₇NO₆S
• Molecular Weight: 385.48
• Mol File: 140645-28-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE(CAS DataBase Reference)
• NIST Chemistry Reference: ((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE(140645-28-9)
• EPA Substance Registry System: ((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE(140645-28-9)

Safety Data

• Hazardous Substances Data: 140645-28-9(Hazardous Substances Data)

Usage

Description

((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE is a sulfonate ester derivative of an oxazolidinylmethyl carbamate with the molecular formula C18H27NO5S. It is a white to off-white solid that is stable under normal conditions and soluble in organic solvents such as dichloromethane and tetrahydrofuran. ((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE plays a crucial role in pharmaceutical and chemical research and development.
Used in Pharmaceutical and Chemical Research and Development:
((S)-3-(TERT-BUTOXYCARBONYL)-2,2-DIMETHYLOXAZOLIDIN-4-YL)METHYL 4-METHYLBENZENESULFONATE is used as a protecting group for amino acids in peptide synthesis. It aids in the synthesis of complex peptides by preventing unwanted side reactions and ensuring the correct formation of peptide bonds. This protecting group is essential for the development of new drugs and the study of peptide-based compounds.

Upstream product

• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 95715-86-9 (S)-2,2-dimethyl-oxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 108149-63-9 4-hydroxymethyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 935547-69-6 4(R)-4-((4-benzylphenoxy)methyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 935547-66-3 4(S)-4-(4-chlorobenzylthiomethyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester 
• 211681-05-9 [(S)-2-(Diphenyl-phosphinothioyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester 
• 943599-10-8 (4S)-N-tert-butoxycarbonyl-4-[(diphenylphosphinoyl)methyl]-2,2-dimethyl-1,3-oxazolidine 
• 952196-93-9 (R)-tert-butyl-N-[3-(4-decyloxyphenoxy)-1-(dimethoxyphosphoryloxy)propan-2-yl]carbamate 
• 952196-92-8 (R)-tert-butyl-N-[1-(dimethoxyphosphoryloxy)-3-(4-propylphenoxy)propan-2-yl]carbamate 
• 952196-91-7 (R)-tert-butyl-N-[3-(4-chloro-3-methylphenoxy)-1-(dimethoxyphosphoryloxy)propan-2-yl]carbamate 
• 952196-90-6 (R)-tert-butyl-N-[3-(4-benzylphenoxy)-1-(dimethoxyphosphoryloxy)propan-2-yl]carbamate 
• 952196-66-6 (R)-tert-butyl-N-[1-(dimethoxyphosphoryloxy)-3-[4-(2-methoxyethyl)phenoxy]propan-2-yl]carbamate 
• 952196-88-2 (S)-tert-butyl-N-[3-(4-chlorobenzylthio)-1-(dimethoxyphosphoryloxy)propan-2-yl]carbamate 
• 952196-84-8 (S)-tert-butyl-N-[3-(4-decyloxyphenoxy)-1-hydroxypropan-2-yl]carbamate 
• 952196-83-7 (S)-tert-butyl-N-[1-hydroxy-3-(4-propylphenoxy)propan-2-yl]carbamate 
• 952196-82-6 (S)-tert-butyl-N-[3-(4-chloro-3-methylphenoxy)-1-hydroxypropan-2-yl]carbamate 
• 952196-81-5 (S)-tert-butyl-N-[3-(4-benzylphenoxy)-1-hydroxypropan-2-yl]carbamate 

Relevant articles and documents

Generating Stereodiversity: Diastereoselective Fluorination and Highly Diastereoselective Epimerization of α-Amino Acid Building Blocks

Diastereoselective fluorination of N-Boc (R)- and (S)-2,2-dimethyl-4-((arylsulfonyl)methyl)oxazolidines and a previously unknown diastereoselective epimerization at the fluorine-bearing carbon atom α to the sulfone was realized. Diastereoselectivities of both reactions were excellent for benzothiazolyl sulfones, allowing access to two enantiomerically pure diastereomers from one chiral precursor. To demonstrate synthetic utility, the benzothiazolyl sulfones were converted to diastereomerically pure (S,S)- and (R,S)-benzyl sulfones via sulfinate salts and to amino acids. To understand the diastereoselectivities, DFT analysis was performed.

Design, synthesis and activity as acid ceramidase inhibitors of 2-oxooctanoyl and N-oleoylethanolamine analogues

The synthesis of novel N-acylethanolamines and their use as inhibitors of the aCDase is reported here. The compounds are either 2-oxooctanamides or oleamides of sphingosine analogs featuring a 3-hydroxy-4,5-hexadecenyl tail replaced by ether or thioether

Synthesis of 2-amino-octa-4,7-dien-1-ol (2): Key intermediate for mycothiazole natural product and analogs

Starting from L-aminoacids, facile methods for the preparation 2-aminocta-4,7-dien-ol with different stereochemistry have been developed as key intermediates of mycothiazole and analogs. Copyright Taylor & Francis, Inc.