140889-07-2

Basic information

• Product Name: (2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene
• Synonyms: (2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene
• CAS NO: 140889-07-2
• Molecular Weight: 446.746
• Mol File: 140889-07-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene(140889-07-2)
• EPA Substance Registry System: (2R,3S,4S,5S,6E)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-6-nonene(140889-07-2)

Safety Data

• Hazardous Substances Data: 140889-07-2(Hazardous Substances Data)

Upstream product

• 623-36-9 (E)-2-methylpent-2-enal 
• 140870-56-0 (2R,4R,5S,6E)-5-hydroxy-2,4,6-trimethyl-1-phenylmethoxy-6-nonen-3-one 
• 85272-31-7 di-tert-butylsilyl bis(trifluoromethanesulfonate) 
• 140870-57-1 (2S,3S,4S,5S,6E)-2,4,6-trimethyl-1-phenylmethoxy-6-nonene-3,5-diol 

Downstream Products

• 87697-98-1 Denticulatin A 
• 140870-58-2 (2R,3S,4S,5R,6R,7R)-2,4,6-trimethyl-3,5-<dioxy>-1-phenylmethoxy-7-nonanol 

Relevant articles and documents

Total synthesis of (-)-denticulatins A and B using efficient methods of acyclic stereocontrol

The total synthesis of (-)-denticulatin B (2) was achieved in 9 steps (20% yield), with 70% overall diastereoselectivity, starting from the ethyl ketone (R)-9. Most of the stereochemistry was introduced by substrate-based control. Key steps include the boron-mediated aldol/reduction, 9 → 22, the titanium-mediated aldol-coupling. 26 + 8 → 38, and the directed cyclisation, 35 → 2. Epimerisation at C10 in 35 led to (-)-denticulatin A (1).