288159-38-6

Basic information

• Product Name: Carbamic acid, [(1S)-1-(hydroxymethyl)-2-methyl-2-propenyl]-, 1,1-
• Synonyms: Carbamic acid, [(1S)-1-(hydroxymethyl)-2-methyl-2-propenyl]-, 1,1-
• CAS NO: 288159-38-6
• Molecular Formula: C₁₀H₁₉NO₃
• Molecular Weight: 201.26276
• Product Categories: N-BOC
• Mol File: 288159-38-6.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Carbamic acid, [(1S)-1-(hydroxymethyl)-2-methyl-2-propenyl]-, 1,1-(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-1-(hydroxymethyl)-2-methyl-2-propenyl]-, 1,1-(288159-38-6)
• EPA Substance Registry System: Carbamic acid, [(1S)-1-(hydroxymethyl)-2-methyl-2-propenyl]-, 1,1-(288159-38-6)

Safety Data

• Hazardous Substances Data: 288159-38-6(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 95715-85-8 2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester 
• 288159-37-5 (4S)-4-(1-Methylethenyl)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine 
• 108149-60-6 methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate 
• 79069-14-0 (S)-2-<(tert-butoxycarbonyl)amino>-3-methylbutan-1-ol 
• 288159-36-4 tert-butyl (4R)-4-(1-hydroxy-1-methylethyl)-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 

Downstream Products

• 488727-81-7 toluene-4-sulfonic acid (2S)-tert-butoxycarbonylamino-3-methyl-but-3-enyl ester 
• 269742-33-8 (2S)-2-(N-tert-Butoxycarbonyl)amino-3-methylbut-3-enoic acid 

Relevant articles and documents

Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives

The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.

Examining the chirality, conformation and selective kinase inhibition of 3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino) piperidin-1-yl)-3-oxopropanenitrile (CP-690,550)

Here, we examine the significance that stereochemistry plays within the clinically relevant Janus kinase 3 (Jak3) inhibitor 1 (CP-690,550). A synthesis of all four enantiopure stereoisomers of the drug was carried out and an examination of each compound revealed that only the enantiopure 3R,4R isomer was capable of blocking Stat5 phosphorylation (Jak3 dependent). Each compound was profiled across a panel of over 350 kinases, which revealed a high level of selectivity for the Jak family kinases for these related compounds. Each stereoisomer retained a degree of binding to Jak3 and Jak2 and the 3R,4S and 3S,4R stereoisomers were further revealed to have binding affinity for selected members of the STE7 and STE20 subfamily of kinases. Finally, an appraisal of the minimum energy conformation of each stereoisomer and molecular docking at Jak3 was performed in an effort to better understand each compounds selectivity and potency profiles.

Facile synthesis of L-3,4-didehydrovaline constituting an antibiotic, phomopsin A

A convenient synthesis of δ,γ-unsaturated valine (L-3,4- didehydrovaline), an important constituent of an antibiotic phomopsin A, was achieved from H-D-Ser-OH through a seven-step conversion in 31percent overall yield.