116911-14-9

Basic information

• Product Name: (2S,3S)-3-azido-3-phenylpropane-1,2-diol
• Synonyms: (2S,3S)-3-Azido-3-phenyl-1,2-propanediol; (2S,3S)-3-Azido-3-phenylpropane-1,2-diol; 1,2-propanediol, 3-azido-3-phenyl-, (2S,3S)-
• CAS NO: 116911-14-9
• Molecular Formula: C₉H₁₁N₃O₂
• Molecular Weight: 193.2025
• Mol File: 116911-14-9.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-azido-3-phenylpropane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-azido-3-phenylpropane-1,2-diol(116911-14-9)
• EPA Substance Registry System: (2S,3S)-3-azido-3-phenylpropane-1,2-diol(116911-14-9)

Safety Data

• Hazardous Substances Data: 116911-14-9(Hazardous Substances Data)

Upstream product

• 99528-63-9 (2S,3R)-2,3-epoxy-3-phenylpropan-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 98819-68-2 3-phenyl-(2R,3R)-oxiran-2-ylmethanol 

Downstream Products

• 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 
• 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 
• 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 
• 1253911-96-4 (3R,E)-3-amino-3-phenyl-1-phenylsulfonyl-1-propene trifluoroacetate salt 

Relevant articles and documents

A practical route to enantiopure 1,2-aminoalcohols

A series of enantiopure aminoalcohols were synthesized from the corresponding diols by activation of the diols as cyclic carbonates, azide opening of the carbonates, and hydrogenation of the resulting azidoalcohols. Factors affecting the azide opening of the carbonates, a simple workup procedure, and a large scale synthesis of (1R,2S)-(-)-2-amino-1,2-diphenylethanol are described.

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.