93472-93-6

Basic information

• Product Name: Carbamic acid, (3-mercaptopropyl)-, 1,1-dimethylethyl ester (9CI)
• Synonyms: Carbamic acid, (3-mercaptopropyl)-, 1,1-dimethylethyl ester (9CI);tert-butyl (3-mercaptopropyl)carbamate
• CAS NO: 93472-93-6
• Molecular Formula: C₈H₁₇NO₂S
• Molecular Weight: 191.29108
• Product Categories: N-BOC
• Mol File: 93472-93-6.mol

Chemical Properties

• Boiling Point: 285.5±23.0 °C(Predicted)
• Appearance: /
• Density: 1.023±0.06 g/cm3(Predicted)
• PKA: 10.29±0.10(Predicted)
• CAS DataBase Reference: Carbamic acid, (3-mercaptopropyl)-, 1,1-dimethylethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, (3-mercaptopropyl)-, 1,1-dimethylethyl ester (9CI)(93472-93-6)
• EPA Substance Registry System: Carbamic acid, (3-mercaptopropyl)-, 1,1-dimethylethyl ester (9CI)(93472-93-6)

Safety Data

• Hazardous Substances Data: 93472-93-6(Hazardous Substances Data)

Upstream product

• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 

Downstream Products

• 1229579-38-7 C₂₄H₃₄N₄O₄S₂ 
• 733053-61-7 {3-[4-(4-methoxy-benzyloxy)-quinolin-2-ylsulfanyl]-propyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

METALLO-BETA-LACTAMASE INHIBITORS

The present invention relates to compounds of formula I that are metallo-β-lactamase inhibitors, the synthesis of such compounds, and the use of such compounds for use with β-lactam antibiotics for overcoming resistance.

Efficient synthesis of five and six member sultam

A robust approach for the synthesis of five and six member sultam is achieved employing commercially available starting materials and reagents. The use of simplest reactions without any critical parameter is the key strength of this route applicable on large scale synthesis.

7-N-(mercaptoalkyl)mitomycins: Implications of cyclization for drug function

The Kyowa Hakko Kogyo and Bristol-Myers Squibb companies reported that select mitomycin C(7) aminoethylene disulfides displayed improved pharmacological profiles compared with mitomycin C (1). Mechanisms have been advanced for these mitomycins that differ from 1. Central to many of these hypotheses is the intermediate generation of 7-N-(2-mercaptoethyl)mitomycin C (5). Thiol 5 has been neither isolated nor characterized. Two efficient methods were developed for mitomycin (porfiromycin) C(7)-substituted thiols. In the first method, the thiol was produced by a thiol-mediated disulfide exchange process using an activated mixed mitomycin disulfide. In the second route, the thiol was generated by base-mediated cleavage of a porfiromycin C(7)-substituted thiol ester. We selected four thiols, 7-N-(2-mercaptoethyl)mitomycin C (5), 7-N-(2-mercaptoethyl)porfiromycin (12), 7-N-(2-mercapto-2-methylpropyl)mitomycin C (13), and 7-N-(3-mercaptopropyl)porfiromycin (14), for study. Thiols 5 and 12-14 differed in the composition of the alkyl linker that bridged the thiol with the mitomycin (porfiromycin) C(7) amino substituent. Thiol generation was documented by HPLC and spectroscopic studies and by thiol-trapping experiments. The linker affected the structure of the thiol species and the stability of the thiol. We observed that thiols 5 and 12 existed largely as their cyclic isomers. Evidence is presented that cyclization predominantly occurred at the mitomycin C(7) position. Correspondingly, alkyl linker substitution (13) or extension of the linker to three carbons (14) led to enhanced thiol stability and the predominant formation of the free thiol species. The dominant reaction of thiols 5 and 12-14 or their isomers was dimerization, and we found no evidence that thiol formation led to mitosene production and aziridine ring-opening. These findings indicated that thiol generation was not sufficient for mitomycin ring activation. The potential pharmacological advantages of mitomycin C(7) aminoethylene disulfides compared with 1 is discussed in light of the observed thiol cyclization pathway.