144067-05-0

Basic information

• Product Name: (3aS,4S,5R,7aR)-5,7a-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one
• Synonyms: (3aS,4S,5R,7aR)-5,7a-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one
• CAS NO: 144067-05-0
• Molecular Weight: 442.743
• Mol File: 144067-05-0.mol

Chemical Properties

• CAS DataBase Reference: (3aS,4S,5R,7aR)-5,7a-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3aS,4S,5R,7aR)-5,7a-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one(144067-05-0)
• EPA Substance Registry System: (3aS,4S,5R,7aR)-5,7a-Bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxymethyl-4-methyl-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one(144067-05-0)

Safety Data

• Hazardous Substances Data: 144067-05-0(Hazardous Substances Data)

Upstream product

• 496-64-0 3-hydroxy-2-pyrone 

Relevant articles and documents

Total synthesis of Taxol. 2. Construction of A and C ring intermediates and initial attempts to construct the ABC ring system

A method for the formation of Taxol's ABC ring system has been developed. General methods for the synthesis of versatile synthons for Taxol's A ring (8) and C ring (55) are presented. A model study using a simplified C ring synthon (17) confirmed the viability of the sequential Shapiro-McMurry strategy for formation of Taxol's B ring. Careful exploration of the chemistry of various A-B ring conjugates allowed the development of a successful method for formation of the B ring in a more functionalized system.

Synthesis of a Fully Functionalized CD Ring System of Taxol

Key building blocks 16 and 17 related to taxol CD ring system have been synthesized in racemic form via a stereocontrolled and efficient sequence featuring a novel Diels-Alder reaction and oxetane formation.