92506-79-1

Basic information

• Product Name: (R)-2-((R)-1-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid methyl ester
• CAS NO: 92506-79-1
• Molecular Weight: 438.545
• Mol File: 92506-79-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (R)-2-((R)-1-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-((R)-1-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid methyl ester(92506-79-1)
• EPA Substance Registry System: (R)-2-((R)-1-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-thiazolidine-4-carboxylic acid methyl ester(92506-79-1)

Safety Data

• Hazardous Substances Data: 92506-79-1(Hazardous Substances Data)

Upstream product

• 106930-50-1 Z-D-Glu-(O-t-Bu)-O-t-Bu 
• 106930-52-3 tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}-5-hydroxypentanoate 
• 63648-73-7 N-benzyloxycarbonyl-D-glutamic acid 
• 2485-62-3 L-Cysteine methyl ester 
• 92506-78-0 (R)-4-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester 
• 56877-41-9 methyl 2(S)-2-benzyloxycarbonylamino-4-tert-butoxycarbonylbutanoate 
• 106930-52-3 S-4-benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester 
• 92506-78-0 4(S)-benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester 

Downstream Products

• 95716-09-9 Z-L-(glu)Thz-OMe 
• 106930-64-7 Z-D-(gln)Thz-OMe 
• 92506-82-6 Z-(gly)Thz-L-Pro-L-Leu-L-Val-L-(gln)Thz-OMe 
• 95716-10-2 Z-L-(glu)Thz-OH 
• 106930-63-6 Z-D-Thz-O-Me 
• 95716-08-8 Z-L-Thz-O-Me 
• 95716-08-8 Z-L-(glu(OBu^t))Thz-OMe 

Relevant articles and documents

New Methods and Reagents in Organic Synthesis. 67. A General Synthesis of Derivatives of Optically Pure 2-(1-Aminoalkyl)thiazole-4-carboxylic Acids

Preparations of 2-(1-aminoalkyl)thiazole-4-carboxylic acids (thiazole amino acids), important constituents of a series of cytotoxic cyclic peptides from marine organisms, have been conveniently and efficiently achieved as their N- and C-protected derivatives 6 from N-Boc or N-Z α-amino acids 1 in five steps.Esterification of 1 with methyl iodide followed by reduction with lithium chloride-sodium borohydride afforded N-protected amino alcohols 3.Selective reduction of the α-ester functions of the glutamic acid derivatives (Z-D- and Z-L-Glu(O-t-Bu)-OMe and O-t-Bu) was also achieved under the above reduction conditions.Dimethyl sulfoxide oxidation, followed by condensation with cysteine methyl ester afforded the thiazolidine derivatives 5, which were conveniently dehydrogenated with manganese dioxide, called chemical manganese dioxide (CMD) and produced for batteries, to give the desired thiazole amino acid derivetives 6.The glutamine derivatives (Z-D- and Z-L-(gln)Thz-OMe) were prepared from the corresponding glutamic acid derivatives (Z-D- and Z-L-6f).No appreciable racemization was observed in the above conversion, which was proven by HPLC of the 3,5-dinitrobenzoyl derivatives of thiazole amino acids 6 using a chiral column.