5817-02-7

Basic information

• Product Name: (2RS,3RS)-3-amino-3-phenyl-propane-1,2-diol
• CAS NO: 5817-02-7
• Molecular Weight: 167.208
• Mol File: 5817-02-7.mol

Chemical Properties

• CAS DataBase Reference: (2RS,3RS)-3-amino-3-phenyl-propane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2RS,3RS)-3-amino-3-phenyl-propane-1,2-diol(5817-02-7)
• EPA Substance Registry System: (2RS,3RS)-3-amino-3-phenyl-propane-1,2-diol(5817-02-7)

Safety Data

• Hazardous Substances Data: 5817-02-7(Hazardous Substances Data)

Upstream product

• 125414-35-9 (4R,5S)-5-hydroxy-4-phenyl-2-(trichloromethyl)-5,6-dihydro-4H-oxazine 
• 21915-53-7 (2R,3S)-(3-phenyloxiran-2-yl)methanol 
• 125414-22-4 2,2,2-Trichloro-acetimidic acid (2R,3S)-3-phenyl-oxiranylmethyl ester 
• 888716-49-2 (+)-(2R,3S)-isopropyl 3-(benzyloxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 121745-64-0 (2R,3S)-3-azido-3-phenylpropane-1,2-diol 
• 18652-74-9 erythro-2-bromo-3-hydroxy-3-phenylpropan-1-ol 
• 77790-77-3 3-Phenyl-4,5-dihydro-isoxazol-4-ol 
• 36808-12-5 rac-(2R,3S)-2,3-dibromo-3-phenylpropan-1-ol 

Downstream Products

• 125414-45-1 (2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol 
• 897054-33-0 (+)-(3'S,4'S)-2-(3'-phenyl-4'-hydroxymethyl-3',4'-dihydrooxazol-2'-yl)aniline 
• 103150-32-9 (1S,2R)-N-1-(1-phenyl-2,3-dihydroxypropyl)benzamide 

Relevant articles and documents

Concise synthesis of the Taxol side chain and demethoxy-4-epi-cytoxazone via oxazoline formation through intramolecular benzylic substitution of a bis-trichloroacetimidate

A concise and efficient method for synthesizing the Taxol side chain via the corresponding oxazoline intermediate was developed. The oxazoline ring is formed via an SN1 mechanism to ensure that the trans-oxazoline stereochemistry is retained. This process was induced by intramolecular benzylic substitution of a 1,2-bis-trichloroacetimidate, which was obtained from a known, enantiomerically pure diol. Demethoxy-4-epi-cytoxazone was also obtained from the intermediary trans-oxazoline 3b.

Synthesis of the Neurokinin 1 Receptor Antagonist (+)-L-733,060 by Jacobsen’s Hydrolytic Kinetic Resolution

Abstract: Enantioselective synthesis of the neurokinin 1 receptor antagonist (+)-L-733,060 has been achieved using Jacobsen’s hydrolytic kinetic resolution strategy. Intermediate tert-butyl (2S,3S)-3-hydroxy-2-phenylpiperidine-1-carboxylate has been synthesized with an overall yield of 10.25% and more than 98% ee via sequential reactions starting from cinnamyl alcohol and using Grubbs metathesis in the final stage.

Asymmetric synthesis of novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluation of their anti-inflammatory activity

Aims: To design and synthesize novel N-(1-phenyl-2,3-dihydroxypropyl) arachidonylamides and evaluate their analgesic and anti-inflammatory potential. Main methods: The murine macrophage cell line RAW 264.7 has been widely used as a model for inflammatory responses in vitro. Our model consists of cultured monolayers of RAW 264.7 cells in which media concentrations of 15-deoxy-Δ13,14-PGJ2 (PGJ) are measured by ELISA following LPS (10 ng/ml) stimulation and treatment with 0.1, 0.3, 1.0, 3.0 and 10 μM concentrations of the compounds. Key findings: Our data indicate that several of our compounds have the capacity to increase production of PGJ and may also increase the occurrence of programmed cell death (apoptosis). Significance: Thus these agents are potential candidates for the therapy of conditions characterized by ongoing (chronic) inflammation and its associated pain.

Amino Acids and Peptides; 70. Optically Active α-Amino Acids, N-Boc-Aminoaldehydes and α-Amino-β-hydroxy Acids from 2,3-Epoxy Alcohols

Trichloroacetimidic esters of 2,3-epoxy alcohols are transformed into oxazolines 5 and dihydrooxazines 6, respectively, depending on the structure of the educts and the catalyst.The five-membered ring compounds 5 are transformed into erythro-α-amino-β-hydroxy acids (60-70percent from epoxy alcohols) via axazolidinones 11, 12, and 13. α-Amino acids and α-substituted α-amino acids 10 as well as the corresponding aldehydes 9 are obtained from the dihydrooxazines 6 (50-60percent from epoxy alcohols).