635727-02-5

Basic information

• Product Name: (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol
• Synonyms: (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol
• CAS NO: 635727-02-5
• Molecular Weight: 288.387
• Mol File: 635727-02-5.mol

Chemical Properties

• CAS DataBase Reference: (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol(635727-02-5)
• EPA Substance Registry System: (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol(635727-02-5)

Safety Data

• Hazardous Substances Data: 635727-02-5(Hazardous Substances Data)

Upstream product

• 99493-25-1 diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate) 
• 635726-99-7 (1S)-1-(2,2,5-trimethyl-1,3-dioxan-5-yl)but-3-en-1-ol 
• 138517-53-0 5-(2,2,5-trimethyl-1,3-dioxane)carbaldehyde 
• 3663-46-5 5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane 
• 635727-00-3 {(2R,4S,5S)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl}methanol 

Downstream Products

• 635727-25-2 (2R,4S,5R,6R)-6-[2-(tert-butyldimethylsilanyloxy)-ethyl]-5-(tert-butyldimethylsilanyloxymethyl)-5-methyl-4-triethylsilanyloxytetrahydropyran-2-ylmethyl benzoate 
• 635727-24-1 benzoic acid 6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester 
• 635727-23-0 Benzoic acid (2R,4aR,5R,7R,8aS)-5-(2-hydroxy-ethyl)-4a-methyl-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethyl ester 
• 635727-22-9 (2R,4aR,5R,7R)-5-allyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxan-7-ylmethyl benzoate 
• 635727-04-7 (2R,4S,5S,6R)-4-hydroxy-6-(2-hydroxyethyl)-5-hydroxymethyl-5-methyltetrahydropyran-2-ylmethyl benzoate 
• 635727-03-6 (2R,4aR,5R,7R)-5-allyl-7-iodomethyl-4a-methyl-2-phenyltetrahydropyrano[4,3-d][1,3]dioxane 

Relevant articles and documents

Stereoselective total synthesis of the natural (+)-lasonolide A

The natural (+)-lasonolide A (1), an anti-tumor agent, has been synthesized via thermodynamic benzylidene formation at the C22 quaternary chiral center, use of a disulfone equivalent for elongation of the C 15-C17 three-carbon chain as well as introduction of the two trans olefins at C15 and C17, iodocyclization for the upper THP, Michael addition for the bottom THP, and intramolecular Horner-Emmons olefination for the 20-membered macrolactone.

Total Synthesis of Natural (+)-Lasonolide A

The diastereoselective differentiation of two methylene groups of a cyclic acetal is a unique feature of a highly enantioselective total synthesis of natural (+)-Iasonolide A (see picture), which is used to create the C22 quaternary asymmetric center. Other key strategies are the use of a sulfone-sulfide as a three-carbon fragment with two latent trans double bonds and macrocyclization through an intramolecular Horner-Emmons reaction.