141321-50-8

Basic information

• Product Name: tert-butyl (1S,2R)-1-(hydroxymethyl)-2-methylbutylcarbamate
• Synonyms: tert-butyl (1S,2R)-1-(hydroxymethyl)-2-methylbutylcarbamate
• CAS NO: 141321-50-8
• Molecular Weight: 217.309
• Mol File: 141321-50-8.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: tert-butyl (1S,2R)-1-(hydroxymethyl)-2-methylbutylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1S,2R)-1-(hydroxymethyl)-2-methylbutylcarbamate(141321-50-8)
• EPA Substance Registry System: tert-butyl (1S,2R)-1-(hydroxymethyl)-2-methylbutylcarbamate(141321-50-8)

Safety Data

• Hazardous Substances Data: 141321-50-8(Hazardous Substances Data)

Upstream product

• 73-32-5 L-isoleucine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 88996-94-5 (2S,3R)-(+)-isoleucinol 
• 73-32-5 L-isoleucine 
• 2577-46-0 methyl L-isoleucinate 
• 1509-34-8 D-allo-isoleucine 
• 13139-16-7 Boc-L-aIle-OH 
• 132149-82-7 ((2S,3S)-2-Methoxymethoxy-3-methyl-pentyloxymethyl)-benzene 
• 56577-28-7 methyl (2S,3S)-2-hydroxy-3-methylpentanoate 
• 1509-35-9 D-alloisoleucine 
• 13139-16-7 N-tert-butoxycarbonyl-D-alloisoleucine 
• 132149-83-8 ((1R,2S)-1-Benzyloxymethyl-2-methyl-butyl)-carbamic acid tert-butyl ester 
• 2577-46-0 L-isoleucine methyl ester 
• 66866-47-5 Boc-Ile-O-COOiBu 

Downstream Products

• 1334510-21-2 Boc-Ileψ[CH2N(Nos)]Gly-OEt 
• 118656-50-1 5-phenylthiooxazolidin-2-one 
• 132149-75-8 (4R,5R)-4-sec-Butyl-2-oxo-5-phenylsulfanyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 1380336-92-4 tert-butyl ((2R,3S)-3-methyl-1-(4-(4-nitrophenyl)-1H-1,2,3-triazol-1-yl)pentan-2-yl)carbamate 
• 1380336-91-3 tert-butyl ((2R,3S)-1-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-3-methylpentan-2-yl)carbamate 
• 1380336-90-2 tert-butyl ((2R,3S)-3-methyl-1-(4-phenyl-1H-1,2,3-triazol-1-yl)pentan-2-yl)carbamate 
• 132149-84-9 ((1R,2S)-2-Methyl-1-phenylsulfanylmethyl-butyl)-carbamic acid tert-butyl ester 
• 87694-55-1 Boc-D-allo-isoleucinal 

Relevant articles and documents

Urea based foldamers

N,N′-linked oligoureas are a class of enantiopure, sequence-defined peptidomimetic oligomers without amino acids that form well-defined and predictable helical structures akin to the peptide α-helix. Oligourea-based foldamers combine a number of features—such as synthetic accessibility, sequence modularity, and folding fidelity—that bode well for their use in a range of applications from medicinal chemistry to catalysis. Moreover, it was recently recognized that this synthetic helical backbone can be combined with regular peptides to generate helically folded peptide-oligourea hybrids that display additional features in terms of helix mimicry and protein-surface recognition properties. Here we provide detailed protocols for the preparation of requested monomers and for the synthesis and purification of homo-oligoureas and peptide-oligourea hybrids.

Design, synthesis, and structure-activity relationship studies of L-amino alcohol derivatives as broad-spectrum antifungal agents

To discover broad spectrum antifungal agents, two strategies were applied, and a novel class of L-amino alcohol derivatives were designed and synthesized. 3-F substituted compounds 14i, 14n, 14s and 14v exhibited excellent antifungal activities with broad antifungal spectra against C. albicans and C. tropicalis, with MIC values in the range of 0.03–0.06 μg/mL, and against A. fumigatus and C. neoformans, with MIC values in the range of 1–2 μg/mL. Notably, Compounds 14i, 14n, 14s and 14v also displayed moderate activities against fluconazole-resistance strains 17# and CaR that were isolated from AIDS patients. Moreover, only compounds in the S-configuration showed antifungal activity. Preliminary mechanistic studies showed that the potent antifungal activity of compound 14v stemmed from inhibition of C. albicans CYP51. Compounds 14n and 14v were almost nontoxic to mammalian A549 cells, and their stability in human plasma was excellent.

Synthesis and biological activity evaluation of dolastatin 10 analogues with N-terminal modifications

We have described the synthesis of the two complex units (2R,3R,4S)-dolaproine (Dap) and (3R,4S,5S)-dolaisoleuine (Dil) of dolastatin 10 from natural amino acids. The stereoselective syntheses of N-Boc-Dap (4a) and N-Boc-(2S)-iso-Dap (4b) were performed by employing crotylation of N-Boc-L-prolinal as a key step. Barbier-type allylation of N-Boc-L-isoleucinal provided a mild and convenient approach for the synthesis of N-Boc-Dil (5a) and N-Boc-(3S)-iso-Dil (5b). Ten dolastatin 10 analogues have been designed and synthesized with N-terminal modifications based on the known compound monomethylauristatin F (MMAF, 3). In comparison with MMAF (3), four of the compounds showed enhanced potency against HCT 116 human colon cancer cells in?vitro.