670254-71-4

Basic information

• Product Name: (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate
• Synonyms: (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate;(2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate
• CAS NO: 670254-71-4
• Molecular Formula: C₂₃H₂₇NO₆
• Molecular Weight: 413.46
• Mol File: 670254-71-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 100-102 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• Boiling Point: 527.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.188±0.06 g/cm3(Predicted)
• PKA: -4.51±0.70(Predicted)
• CAS DataBase Reference: (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate(670254-71-4)
• EPA Substance Registry System: (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate(670254-71-4)

Safety Data

• Hazardous Substances Data: 670254-71-4(Hazardous Substances Data)

Usage

Description

(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 4S and 5R positions, which give it specific stereochemical properties. (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate features a tert-butoxycarbonyl group, an anisyl group, and a phenyl group, all of which contribute to its chemical reactivity and potential applications.

Uses

Used in Pharmaceutical Industry:
(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Anti-tumor Compound Preparation:
(4S,5R)-3-tert-butoxycarbony-2-(4-anisy)-4-phenyl-5-oxazolidinecarboxylate is used as a starting material for the preparation of anti-tumor compounds based on the docetaxel side chain 2''-derivative. Its incorporation into these compounds may enhance their anti-cancer properties and provide new treatment options for patients with various types of cancer.

Upstream product

• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 123-11-5 4-methoxy-benzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 

Downstream Products

• 125354-16-7 10-acetyldocetaxel 
• 1246748-59-3 C₆₆H₇₃NO₁₆Si 
• 1246748-58-2 C₆₆H₇₅NO₁₆Si 
• 859498-31-0 C₅₇H₆₁Cl₆NO₁₉ 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 114915-20-7 Docetaxel 
• 196404-55-4 acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique 

Relevant articles and documents

Docetaxel side chain 2'-derived novel taxanes antitumor compound as well as synthesis method and application thereof

The invention discloses a docetaxel side chain 2'-derived novel taxanes antitumor compound shown as the general structure formula (I) as well as a synthesis method and application thereof. In the formula, X is N or O, R is H or acetyl, and R' is H, nitryl, cyano, methoxyl or a halogen group. The synthesis method takes 10-deacetylbaccatin is used as a raw material; after 7-OH and 10-OH are protected, condensation with phenylisoserine (side chain) protecting 3'-NHBoc and 2'-OH in the presence of condensation agents DCC (Dicyclohexylcarbodiimide) and DMAP (Dimethylaminopyridine) is performed; esterification with substituted phenyl isoxazole carboxylic acid or substituted phenyl oxadiazole methyl carboxylic acid in the presence of the DCC and the DMAP is performed; finally, a protecting group is removed to obtain the compound. The compound disclosed by the invention has relatively high activity on tumor cells.

A novel method to synthesize docetaxel and its isomer with high yields

Side chains of docetaxel and its isomer were obtained through Staudinger cycloaddition and catalytic hydrogenation of chlorophenyl intermediates, using chlorobenzaldehyde as starting material. Syntheses of three novel chiral azetidinone derivatives through the Staudinger cycloaddition reaction of chlorophenyl chiral amine Schiff base with different substituted positions were described and their ring-opening reaction under the catalysis of Pd/MgCO 3 or Pd/C to afford side chains of docetaxel and its isomer in high yields was investigated. Finally, docetaxel and its isomer were obtained. Single crystal of (3S,4R)-3-hydroxy-N-[(S)(1-phenyl)ethyl]-4 -(2′-chlorophenyl) -2-azetidinone (4c) was obtained, the configuration of which was determined by X-ray diffraction. Because of the mild cyclization reaction condition and convenient asymmetric resolution operation when p-chlorobenzaldehyde was employed instead of benzaldehyde, the yield of cyclization and hydrogenation increased dramatically and the total yield of docetaxel was higher than the result in literature. When o-chlorobenzaldehyde was employed instead of benzaldehyde an isomer of docetaxel was obtained by the same way.