276673-02-0

Basic information

• Product Name: (4R,5S)-5-hydroxy-4-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohex-1-ene-1-carbaldehyde
• Synonyms: (4R,5S)-5-hydroxy-4-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohex-1-ene-1-carbaldehyde
• CAS NO: 276673-02-0
• Molecular Weight: 230.307
• Mol File: 276673-02-0.mol

Chemical Properties

• CAS DataBase Reference: (4R,5S)-5-hydroxy-4-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohex-1-ene-1-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-5-hydroxy-4-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohex-1-ene-1-carbaldehyde(276673-02-0)
• EPA Substance Registry System: (4R,5S)-5-hydroxy-4-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohex-1-ene-1-carbaldehyde(276673-02-0)

Safety Data

• Hazardous Substances Data: 276673-02-0(Hazardous Substances Data)

Upstream product

• 276253-30-6 (1S,2R,4S,5Z)-5-[(acetyloxy)methylene]-2-(5-methyl-1-methylenehex-4-en-2-ynyl)cyclohexane-1,4-diol 4-acetate 
• 129932-67-8 oxytoxin 1 

Relevant articles and documents

Highly diastereoselective, biogenetically patterned synthesis of (+)- (1S,6R)-volvatellin (= (+)-(4R,5S)-5-hydroxy-4-(5-methyl-1-methylenehex-4-en- 2-ynyl)cyclohex-1-ene-1-carbaldehyde)

The synthesis of volvatellin (4a), previously isolated from a herbivorous marine mollusk, was achieved with high diastereoselectivity from putative dietary oxytoxin-1 (2). A biogenetically patterned carbonyl-ene route was chosen, proceeding from 2 predominantly via the trans cyclization product 3 without the use of enzymes. This challenges the involvement of enzymes in the formation of 4a in nature. The optical purity and absolute configuration (IS,4S,6R), assigned to 3 from high-field 1H-NMR examination of its Mosher (MTPA) esters 6, was retained on its chemical conversion to (+)-(1S,6R)-configured 4a and is consistent with the (4S) configuration previously established for caulerpenyne (1).