165683-81-8

Basic information

• Product Name: Carbamic acid, [(1S,2S)-2,3-dihydroxy-1-phenylpropyl]-, 1,1-dimethylethyl ester
• CAS NO: 165683-81-8
• Molecular Formula: C14H21NO4
• Molecular Weight: 267.325
• Mol File: 165683-81-8.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S,2S)-2,3-dihydroxy-1-phenylpropyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S,2S)-2,3-dihydroxy-1-phenylpropyl]-, 1,1-dimethylethyl ester(165683-81-8)
• EPA Substance Registry System: Carbamic acid, [(1S,2S)-2,3-dihydroxy-1-phenylpropyl]-, 1,1-dimethylethyl ester(165683-81-8)

Safety Data

• Hazardous Substances Data: 165683-81-8(Hazardous Substances Data)

Upstream product

• 99528-63-9 (2S,3R)-2,3-epoxy-3-phenylpropan-1-ol 
• 188200-12-6 Benzyl-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-amine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 192764-07-1 N-Benzyl-N-[(S)-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-phenyl-methyl]-hydroxylamine 
• 100-58-3 phenylmagnesium bromide 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 
• 5877-56-5 (E)-N-benzylidene-2-methoxybenzenamine 
• 919770-20-0 (R)-5-((S)-((2-methoxyphenyl)amino)(phenyl)methyl)furan-2(5H)-one (7j). 
• 919770-42-6 5-(amino-phenyl-methyl)-5H-furan-2-one 
• 919770-46-0 [(5-oxo-2,5-dihydro-furan-2-yl)-phenyl-methyl]-carbamic acid tert-butyl ester 
• 188200-13-7 (2S,3S)-3-(tert-butoxycarbonylamino)-1,2-O-isopropylidene-3-phenyl-1,2-propanediol 

Downstream Products

• 165683-83-0 (2S,3S)-3-tert-butoxycarbonylamino-1-tert-butyldimethylsilyloxy-3-phenyl-2-propanol 
• 1253912-09-2 N-((S)-1-oxo-3-phenyl-1-((R,E)-1-phenyl-3-(phenylsulfonyl)allylamino)propan-2-yl)morpholine-4-carboxamide 
• 1253912-20-7 N-((S)-4-methyl-1-oxo-1-((R,E)-1-phenyl-3-(phenylsulfonyl)allylamino)pentan-2-yl)morpholine-4-carboxamide 
• 1253911-96-4 (3R,E)-3-amino-3-phenyl-1-phenylsulfonyl-1-propene trifluoroacetate salt 
• 1253912-41-2 4-methyl-N-((S)-4-methyl-1-oxo-1-((R,E)-1-phenyl-3-(phenylsulfonyl)allylamino)pentan-2-yl)piperazine-1-carboxamide 
• 1253912-31-0 4-methyl-N-((S)-1-oxo-3-phenyl-1-((R,E)-1-phenyl-3-(phenylsulfonyl)allylamino)propan-2-yl)piperazine-1-carboxamide 
• 1262535-96-5 (4S,5S)-5-(hydroxymethyl)-4-phenyloxazolidin-2-one 
• 174283-00-2 tert-butyl (1S,2R)-3-(tert-butyldimethylsilyloxy)-2-hydroxy-1-phenylpropylcarbamate 
• 174282-99-6 (2R,3S)-1-tert-butyldimethylsilyloxy-3-tert-butoxycarbonylamino-2-p-nitrophenylcarbonyloxy-3-phenylpropane 
• 681125-79-1 (2R,3S)-3-phenyl-3-(tert-butoxycarbonylamino)-2-(1-ethoxyethoxy)propionic acid 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 178421-77-7 (4S,5R)-3-(tert-butoxycarbonyl)-5-cyanomethyl-4-phenyl-2,2,-dimethyl-1,3-oxazolidine 
• 178743-89-0 (4S,5R)-5-Carboxymethyl-2,2-dimethyl-4-phenyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 178421-76-6 (3R,4S)-4-(tert-butoxycarbonylamino)-4-phenyl-3-hydroxybutanenitrile 

Relevant articles and documents

Novel peptidyl aryl vinyl sulfones as highly potent and selective inhibitors of cathepsins L and B

Herein we present the design, synthesis, and evaluation of a structurally novel library of 20 peptidyl 3-aryl vinyl sulfones as inhibitors of cathepsins L and B. The building blocks, described here for the first time, were synthesized in a highly efficient and enantioselective manner, starting from 3-aryl-substituted allyl alcohols. The corresponding vinyl sulfones were prepared by a new approach, based on a combination of solid-phase peptide synthesis using the Fmoc/tBu strategy, followed by solution-phase coupling to the corresponding (R)-3-amino-3-aryl vinyl sulfones as trifluoroacetate salts. The inhibitory activity of the resulting compounds against cathepsins L and B was evaluated, and the compound exhibiting the best activity was selected for enzymatic characterization. Finally, docking studies were performed in order to identify key structural features of the aryl substituent.

Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones

A set of diversely substituted N-Boc-γ-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of α-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given γ-amino vinyl sulfone can be obtained with equal ease.

Stereocontrolled addition of Grignard reagents to α-alkoxy nitrones. Synthesis of syn and anti 3-amino-1,2-diols

The stereoselective addition of Grignard reagents to α-alkoxy nitrones has been achieved with excellent stereocontrol using ZnBr2 and Et2AlCl as precomplexing agents to obtain the corresponding syn- and anti- adducts, respectively. The obtained hydroxylamines have been transformed into valuable 3-amino-1,2-diols.