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

Description

N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER, with the CAS number 143527-75-7, is an off-white solid compound that is primarily utilized in the field of organic synthesis. It is a derivative of isoserine, which is an important building block for the synthesis of various biologically active molecules, including pharmaceuticals and agrochemicals.

Uses

Used in Pharmaceutical Industry:
N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER is used as a key intermediate for the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, such as those targeting cancer, inflammation, and other diseases.
Used in Agrochemical Industry:
In the agrochemical industry, N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER is used as a precursor for the development of novel bioactive molecules with potential applications in pest control, crop protection, and other agricultural areas. Its versatility in organic synthesis enables the creation of new compounds with improved efficacy and selectivity.
Used in Organic Synthesis Research:
N-(T-BOC)-3-PHENYL ISOSERINE ETHYL ESTER is also used as a research tool in the field of organic synthesis. Its unique properties and reactivity make it an attractive candidate for the development of new synthetic methods, catalysts, and reaction pathways, which can be applied to a wide range of chemical transformations.

Upstream product

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

Downstream Products

• 143527-74-6 ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 114915-16-1 10-deacetyl-7,10-diTroc-baccatin III 
• 114915-20-7 Docetaxel 
• 33069-62-4 taxol 
• 114915-15-0 C₄₃H₄₈Cl₃NO₁₅ 
• 114915-17-2 C₅₀H₅₂Cl₃NO₁₆ 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 143527-73-5 C₅₁H₆₀Cl₃NO₁₇ 
• 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 
• 1395491-92-5 (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropionic acid ethyl ester 

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.