144066-90-0

Basic information

• Product Name: (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester
• Synonyms: (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester
• CAS NO: 144066-90-0
• Molecular Weight: 256.255
• Mol File: 144066-90-0.mol

Chemical Properties

• CAS DataBase Reference: (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester(144066-90-0)
• EPA Substance Registry System: (3aR,4S,5S,7aS)-5,7a-Dihydroxy-4-methyl-1-oxo-1,3,3a,4,5,7a-hexahydro-isobenzofuran-4-carboxylic acid ethyl ester(144066-90-0)

Safety Data

• Hazardous Substances Data: 144066-90-0(Hazardous Substances Data)

Upstream product

• 496-64-0 3-hydroxy-2-pyrone 
• 90177-85-8 4-hydroxy-2-methylbut-2-enoic acid ethyl ester 

Downstream Products

• 144066-91-1 (1R,4R,5S,6R)-4-Benzyloxy-5-benzyloxymethyl-6-methyl-3-oxo-2-oxa-bicyclo[2.2.2]oct-7-ene-6-carboxylic acid ethyl ester 
• 144066-99-9 Methanesulfonic acid (1S,2R,3R,4S,6R)-1-benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-6-hydroxy-3-methyl-cyclohexylmethyl ester 
• 144066-97-7 Acetic acid (1S,2R,3S,4S,5R)-2-acetoxymethyl-2-benzyloxy-3-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-cyclohexyl ester 
• 144066-98-8 (1R,2S,3R,4R,5S)-2-Benzyloxy-3-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxymethyl-4-methyl-cyclohexanol 
• 144067-00-5 (1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-3-methyl-7-oxa-bicyclo[4.2.0]octane 
• 144066-95-5 Acetic acid (4aS,5S,6R,7S,8aR)-6-acetoxymethyl-6-benzyloxy-5-benzyloxymethyl-2,2,4a-trimethyl-hexahydro-benzo[1,3]dioxin-7-yl ester 
• 144066-96-6 Acetic acid (1S,2R,3S,4S,5R)-2-acetoxymethyl-2-benzyloxy-3-benzyloxymethyl-5-hydroxy-4-hydroxymethyl-4-methyl-cyclohexyl ester 
• 144066-94-4 (4aR,5R,6S,7R,8aS)-6-Benzyloxy-5-benzyloxymethyl-6-hydroxymethyl-2,2,4a-trimethyl-hexahydro-benzo[1,3]dioxin-7-ol 
• 144066-92-2 (1R,4R,5S,6S)-4-Benzyloxy-5-benzyloxymethyl-4,6-bis-hydroxymethyl-6-methyl-cyclohex-2-enol 
• 144067-01-6 (1S,2R,3R,4S,6R)-1-Benzyloxy-2-benzyloxymethyl-3-hydroxymethyl-3-methyl-7-oxa-bicyclo[4.2.0]octan-4-ol 

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.