207303-04-6

Basic information

• Product Name: (3R,4S,5S)-6-[(1S)-3,3-diethyl-2,4-dioxolanyl]-3-methoxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-one
• Synonyms: (3R,4S,5S)-6-[(1S)-3,3-diethyl-2,4-dioxolanyl]-3-methoxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-one
• CAS NO: 207303-04-6
• Molecular Weight: 408.535
• Mol File: 207303-04-6.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S,5S)-6-[(1S)-3,3-diethyl-2,4-dioxolanyl]-3-methoxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5S)-6-[(1S)-3,3-diethyl-2,4-dioxolanyl]-3-methoxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-one(207303-04-6)
• EPA Substance Registry System: (3R,4S,5S)-6-[(1S)-3,3-diethyl-2,4-dioxolanyl]-3-methoxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-one(207303-04-6)

Safety Data

• Hazardous Substances Data: 207303-04-6(Hazardous Substances Data)

Upstream product

• 105-13-5 4-Methoxybenzyl alcohol 
• 120157-60-0 (R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde 
• 2746-25-0 p-Methoxybenzyl bromide 
• 214462-02-9 (1S)-1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-ynyl acetate 
• 214462-00-7 1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-yn-1-ol 
• 214462-03-0 1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-yn-1-one 
• 207303-00-2 (2R,3S,4R)-1-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-3-methyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)pentan-2-ol 
• 207303-02-4 (2S,3S,4R)-1-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-3-methyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)pentan-2-ol 
• 207302-94-1 (2R,3S,4E)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-3-methylpent-4-enoic acid 
• 207302-92-9 (1S,2E)-1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-enyl 2-methoxyacetate 
• 207302-91-8 (1S,2E)-1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-en-1-ol 
• 207303-18-2 (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane 
• 207303-19-3 (2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal 
• 207303-03-5 (2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentan-1-ol 

Downstream Products

• 207303-05-7 (4R,5S,6S)-methyl 7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enoate 
• 207303-06-8 (4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal 

Relevant articles and documents

Synthetic studies of antitumor macrolide rhizoxin: Stereoselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits

A triply convergent synthetic approach which culminates in the enantioselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits of the macrolide antitumor agent rhizoxin is described. The central C(12)-C(20) subunit 4 has been prepared efficiently via diastereoselective enzymatic acetate hydrolysis of 15 with porcine pancreatic lipase, a chelation- controlled Ireland-Claisen rearrangement (10 → 12) combined with kinetic bromolactonization (12 → 14), and Mitsunobu inversion (23 → 26) to introduce the three contiguous C(15)-C(17) stereocenters. Formation of the C(18)-C(19) trisubstituted (E)-olefin was achieved by a stereoselective Horner-Wadsworth-Emmons reaction. The central segment 4 and the oxazole chromophore side chain 3 were coupled using another highly stereoselective Horner-Wadsworth-Emmons reaction. Two different lactone subunits [C(1)-C(9) segment 5 and C(3)-C(10) segment 47] were also prepared, employing a thermodynamically controlled diastereotopic group differentiation tactic for establishing the C(5) stereochemistry.

Stereoselective syntheses of the rhizoxin C(1)-C(9) and C(12)-C(26) subunits

Stereoselective syntheses of the C(1)-C(9) and C(12)-C(26) subunits of the macrolide antitumor agent rhizoxin are described. Chelation-controlled Ireland-Claisen rearrangement, stereoselective Horner-Wadsworth-Emmons reactions and a thermodynamically-cont