96929-02-1

Basic information

• Product Name: BOC-L-VALINE THIOAMIDE
• Synonyms: BOC-L-VALINE THIOAMIDE;N-TERT-BUTOXYCARBONYL-L-VALINE THIOAMIDE
• CAS NO: 96929-02-1
• Molecular Formula: C₁₀H₂₀N₂O₂S
• Molecular Weight: 232.34
• Mol File: 96929-02-1.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: BOC-L-VALINE THIOAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-VALINE THIOAMIDE(96929-02-1)
• EPA Substance Registry System: BOC-L-VALINE THIOAMIDE(96929-02-1)

Safety Data

• Hazardous Substances Data: 96929-02-1(Hazardous Substances Data)

Usage

Description

BOC-L-VALINE THIOAMIDE, also known as (S)-[1-(aminothioxomethyl)-2-methylpropyl]-carbamic Acid 1,1-Dimethylethyl Ester, is an organic compound that serves as an intermediate in the synthesis of pharmaceuticals. It is characterized by its unique structure, which includes a thioamide group and a protected amino group, making it a versatile building block in organic synthesis and medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
BOC-L-VALINE THIOAMIDE is used as an intermediate in the synthesis of QZ59S-SSS (Q990000), a potential inhibitor of human P-glycoprotein. This makes it a valuable compound for improving the efficacy of cancer chemotherapy, as it can help overcome multidrug resistance in cancer cells by inhibiting the efflux pump mechanism.

Upstream product

• 35150-08-4 Boc-Val-NH₂ 
• 13734-41-3 t-Boc-L-valine 
• 72-18-4 L-valine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 98807-40-0 Boc-Val-O-COOEt 
• 3014-80-0 (S)-2-amino-3-methylbutanamide hydrochloride 
• 66866-46-4 C₁₅H₂₇NO₆ 

Downstream Products

• 946851-42-9 C₅₈H₆₆N₁₂O₉S₆Si 
• 946851-43-0 C₆₂H₇₁N₁₅O₁₁S₆Si 
• 946851-44-1 (S)-2-[2-methyl-1-(tritylamino)propyl]-thiazole-4-carboxylic acid ethyl ester 
• 946851-45-2 (S)-5-methoxymethyl-2-[2-methyl-1-(tritylamino)propyl]-thiazole-4-carboxylic acid ethyl ester 
• 220717-72-6 2-((S)-1-{[2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-oxazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carboxylic acid 
• 220717-71-5 2-((S)-1-{[2-((S)-1-Benzyloxycarbonylamino-2-methyl-propyl)-oxazole-4-carbonyl]-amino}-2-methyl-propyl)-thiazole-4-carboxylic acid ethyl ester 

Relevant articles and documents

Singlet Oxygen Photooxidation of Peptidic Oxazoles and Thiazoles

Oxazoles and thiazoles are commonly found moieties in nonribosomal peptides (NRPs) and ribosomally synthesized post-translationally modified peptides (RiPPs), which are important biomolecules present in the environment and in natural waters. From previous studies, they seem susceptible to oxidation by singlet oxygen (1O2); therefore, we designed and synthesized model oxazole- and thiazole-peptides and measured their1O2 bimolecular reaction rate constants, showing slow photooxidation under environmental conditions. We reasoned their stability through the electron-withdrawing effect of the carboxamide substituent. Reaction products were elucidated and support a reaction mechanism involving cycloaddition followed by a series of rearrangements. The first1O2 bimolecular reaction rate constant for a RiPP, the thiazole-containing peptide Aerucyclamide A, was measured and found in good agreement with the model peptide's rate constant, highlighting the potential of using model peptides to study the transformations of other environmentally relevant NRPs and RiPPs.

Isolation, Structure Elucidation, Biosynthesis, and Synthesis of Antalid, a Secondary Metabolite from Polyangium species

The isolation, structure elucidation, and synthesis of antalid (1), a novel secondary metabolite from Polyangium sp., is described herein. The structure elucidation of 1 was performed with the aid of mass spectrometry, high field NMR experiments, and crystal structure analysis. The absolute configuration of antalid was confirmed through the Mosher ester method and ultimately by total synthesis. In addition, the biosynthetic origin of this hybrid PKS-NRPS natural product was unraveled by the in silico analysis of its biosynthetic gene cluster.

Synthesis of the thiazole-thiazoline fragment of largazole analogues

The thiazole - thiazoline fragment of the marine natural product largazole, a potent histone deacetylase 1 inhibitor, has been synthesized in five steps. The methodology provides rapid access to thiazole-4-carbonitrile, thiazole-4-carbimidate, thiazole -