143527-75-7

Basic information

• Product Name: N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER
• Synonyms: N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER;(αR,βS)-β-[[(1,1-DiMethylethoxy)carbonyl]aMino]-α-hydroxy-benzenepropanoic Acid Ethyl Ester
• CAS NO: 143527-75-7
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.35752
• Product Categories: Aromatics Compounds;Aromatics;Amino Acids & Derivatives;Amino Acids & Derivatives, Aromatics
• Mol File: 143527-75-7.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Ethyl Acetate, Methanol (Slightly)
• CAS DataBase Reference: N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER(143527-75-7)
• EPA Substance Registry System: N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER(143527-75-7)

Safety Data

• Hazardous Substances Data: 143527-75-7(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

N-(t-Boc)-3-phenyl Isoserine Ethyl Ester (cas# 143527-75-7) is a compound useful in organic synthesis.

Upstream product

• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 481054-46-0 ethyl (2RS,3SR)-3-amino-2-hydroxy-3-phenylpropionate 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 100-52-7 benzaldehyde 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 

Downstream Products

• 1395491-92-5 (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropionic acid ethyl ester 
• 143527-74-6 ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 143527-76-8 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 143527-73-5 C₅₁H₆₀Cl₃NO₁₇ 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 114915-17-2 C₅₀H₅₂Cl₃NO₁₆ 
• 114915-15-0 C₄₃H₄₈Cl₃NO₁₅ 
• 33069-62-4 taxol 
• 114915-20-7 Docetaxel 
• 114915-16-1 10-deacetyl-7,10-diTroc-baccatin III 

Relevant articles and documents

PROCESS FOR PREPARING (2R, 3S) 2-BENZYLOXY-3-TERT-BUTOXY CARBONYL AMINO-3-PHENYL PROPIONIC ACID

A method for preparing(2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropionic acid of formula (I) is provided, and a method for purifying and isolating the compound is also provided. The method uses inexpensive, non-hazardous and easily available reagents and results in better yields and purity.

Stereospecific preparation of glycidic esters from 2-chloro-3-hydroxyesters. Application to the synthesis of (2R,3R)-3-phenylisoserine

Cis- and trans-glycidic esters may be synthesized in high enantiomeric purities by cyclisation with potassium carbonate in DMF of the corresponding syn- or anti-2-chloro-3-hydroxyesters, prepared by microbial reduction of 2-chloro-3-oxoesters. In contrast, more basic media such as sodium ethylate afford exclusively the trans-isomer, whatever the stereochemistry of the starting 2-chloro-3-hydroxyester is. Cyclisation of deuterated compounds showed that this result was due to a rapid isomerisation of the syn esters into anti isomers before cyclisation. An application of this reaction to the synthesis of (2R,3R)-3-phenylisoserine is described.

Improved protection and esterification of a precursor of the taxotere and taxol side chains

(4S,5R)-N-BOC-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a,b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere, taxol and analogs.