(2R,3S)-3-phenylisoserine hydrochloride

Base Information

• Chemical Name: (2R,3S)-3-phenylisoserine hydrochloride
• CAS No.: 132201-32-2
• Molecular Formula: C9H12ClNO3
• Molecular Weight: 217.652
• Hs Code.: 2942000000
• DSSTox Substance ID: DTXSID10564249
• Mol file: 132201-32-2.mol

Synonyms:(2R,3S)-3-phenylisoserine hydrochloride;132201-32-2;(2R,3S)-3-Phenylisoserine HCl;(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid hydrochloride;(2R,3S)-3-amino-2-hydroxy-3-phenylpropanoic acid;hydrochloride;MFCD09750971;(2r,3s)-3-amino-2-hydroxy-3-phenyl-propanoic acid hydrochloride;[(1S,2R)-2-carboxy-2-hydroxy-1-phenylethyl]azanium;chloride;(2R,3S)-3-amino-2-hydroxy-3-phenyl-propanoic acid;Benzenepropanoic acid, beta-amino-alpha-hydroxy-, hydrochloride (1:1), (alphaR,betaS)-;(2R,3S)-3-Phenylisoserine hydrochloride;Benzenepropanoic acid, beta-amino-alpha-hydroxy-, hydrochloride, (alphaR,betaS)- (9CI);Benzenepropanoic acid, beta-amino-alpha-hydroxy-, hydrochloride, [R-(R*,S*)]-;(2R,3S)-3-Phenylisoserine hydrochloride salt;(2R,3S)-3-Phenylisoserinehydrochloride;H-Ise(3-Phenyl)-OH.HCl;SCHEMBL3184809;DTXSID10564249;CHEBI:228837;AMY14655;HY-N2378;AKOS015888978;AC-1998;CS-W023105;DS-1890;(2R,3S)-3-Phenylisoserine hydrochloride, 97%;EN300-7386027;A806393;(2R,3S)-3-Amino-2-hydroxy-3-phenylpropanoic acid--hydrogen chloride (1/1)

Chemical Property of (2R,3S)-3-phenylisoserine hydrochloride

Chemical Property:

• Vapor Pressure: 3.98E-07mmHg at 25°C
• Melting Point: 222-224 ºC (dec.)
• Boiling Point: 400.3oC at 760 mmHg
• Flash Point: 195.9oC
• PSA: 83.55000
• LogP: 1.63420
• Storage Temp.: Inert atmosphere,Room Temperature
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.0505709
• Heavy Atom Count: 14
• Complexity: 178

Purity/Quality:

99% ^*data from raw suppliers

(2R,3S)-3-PhenylisoserineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C(=O)O)O)N.Cl
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H]([C@H](C(=O)O)O)N.Cl
• Uses: (2R,3S)-3-Phenylisoserine Hydrochloride is used in the synthetic preparation of the catalytic asymmetric synthesis of both syn- and anti-β-amino alcohols. (2R,3S)-3-Phenylisoserine Hydrochloride is also used for the synthesis of N-benzoylphenylisoserinates of Lactarius sesquiterpenoid alcohols and is responsible for their antifeedant properties against storage pests.

Technology Process of (2R,3S)-3-phenylisoserine hydrochloride

There total 29 articles about (2R,3S)-3-phenylisoserine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(2R,3S)-3-Amino-2-(tert-butyl-dimethyl-silanyloxy)-3-phenyl-propionic acid isopropyl ester (201339-42-6) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2,161453-08-3,949459-75-0,521059-43-8)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1021/ja973527t

Reference yield: 100.0%

3-Triisopropylsilyloxy-4-phenylazetidin-2-one (132127-31-2,132201-31-1) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2,161453-08-3,949459-75-0,521059-43-8)

Guidance literature:

With hydrogenchloride; at 25 ℃; for 3h;

DOI:10.1016/S0040-4020(01)91210-4

Reference yield: 100.0%

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one (132127-34-5) → (2R,3S)-3-phenylisoserine hydrochloride (132201-32-2,161453-08-3,949459-75-0,521059-43-8)

Guidance literature:

With hydrogenchloride; for 12h; Heating;

DOI:10.1021/jo00005a003

upstream raw materials:

(3R,4S)-3-hydroxy-4-phenylazetidin-2-one

(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one

3-Triisopropylsilyloxy-4-phenylazetidin-2-one

Methyl N-acetyl-3-phenylisoserine

Downstream raw materials:

(4S,5R)-2,4-Diphenyl-4,5-dihydro-oxazole-5-carboxylic acid (4S,4aR)-6,6,8-trimethyl-1-oxo-1,3,4,4a,5,6,7,9-octahydro-2-oxa-cyclopenta[f]azulen-4-yl ester

C₃₁H₃₃NO₆

C₃₁H₃₃NO₆

(2R,3S)-3-Phenyl-1-oxa-4-aza-spiro[4.5]decane-2,4-dicarboxylic acid 2-((4S,4aR,7aS,8S)-8-ethoxy-6,6,8-trimethyl-1-oxo-1,3,4,4a,5,6,7,7a,8,9-decahydro-2-oxa-cyclopenta[f]azulen-4-yl) ester 4-(2,2,2-trichloro-ethyl) ester

Refernces

• 1、 Forró, Eniko,Galla, Zsolt,Nádasdi, Zala,árva, Judit,Fül?p, Ferenc. "Novel chemo-enzymatic route to a key intermediate for the taxol side-chain through enantioselective O-acylation. Unexpected acyl migration". . p. 101 - 105. Retrieved 2015.
• 2、 Forro, Eniko,Fueloep, Ferenc. "A new enzymatic strategy for the preparation of (2R,3S)-3-phenylisoserine: a key intermediate for the Taxol side chain". scheme or table. p. 637 - 639. Retrieved 2010/08/03.