130767-06-5

Basic information

• Product Name: (2S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-4-ene
• Synonyms: (2S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-4-ene
• CAS NO: 130767-06-5
• Molecular Weight: 398.586
• Mol File: 130767-06-5.mol

Chemical Properties

• CAS DataBase Reference: (2S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-4-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-4-ene(130767-06-5)
• EPA Substance Registry System: (2S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-1,7-dioxaspiro<5.5>undec-4-ene(130767-06-5)

Safety Data

• Hazardous Substances Data: 130767-06-5(Hazardous Substances Data)

Upstream product

• 130767-17-8 (7E,12E)-(2R,3S,10S,15R)-16-Benzyloxy-2,10-dihydroxy-3,13,15-trimethyl-hexadeca-7,12-dien-6-one 
• 130767-07-6 (E)-(2R,3S,10R,15R)-16-Benzyloxy-6-methoxy-3,13,15-trimethyl-hexadeca-6,7,12-triene-2,10-diol 
• 86951-92-0 (2S)-3-Benzyloxy-2-methyl-1-p-(toluenesulphonyloxy)propane 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 
• 125131-14-8 (4S,5R)-4-Methyl-5-(p-nitrobenzoyloxy)-1-hexene 
• 125131-19-3 (4E)-(2R,7R)-8-Benzyloxy-1-chloro-5,7-dimethyl-4-octene-2-ol 
• 125131-20-6 (4E)-(2R,7R)-1-Benzyloxy-2,4-dimethyl-7,8-epoxy-4-octene 
• 125131-18-2 (6S,7R)-7-(tert-Butyldimethylsiloxy)-3-methoxy-6-methyl-1,2-octadiene 
• 101906-25-6 (2R)-benzyl-(2-methylpent-4-ynyl) ether 
• 125131-15-9 (4S,5R)-5-(tert-Butyldimethylsiloxy)-4-methyl-1-hexene 
• 125131-16-0 (3S,4R)-4-(tert-Butyldimethylsiloxy)-3-methylpentan-1-ol 
• 125131-17-1 (3S,4R)-4-(tert-Butyldimethylsiloxy)-1-iodo-3-methylpentane 
• 125225-81-2 (2R,3S)-3-Methyl-5-hexen-2-ol 
• 125225-80-1 (2S,3S)-3-Methyl-5-hexen-2-ol 

Downstream Products

• 101906-21-2 [(2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-dimethyl-silane 
• 101906-21-2 (2R,4R,6S,8R,9S)-2-<(5R)-(2E)-6-benzyloxy-3,5-dimethyl-hex-2-en-1-yl>-8,9-dimethyl-4-(dimethyl-t-butylsilyloxy)-1,7-dioxaspiro<5.5>undecane 
• 101906-32-5 (2S,4S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane 
• 101906-32-5 (2R,4R,6R,8R,9S)-2-((E)-(R)-6-Benzyloxy-3,5-dimethyl-hex-2-enyl)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undecan-4-ol 

Relevant articles and documents

A NEW APPROACH TO 1,7-DIOXASPIROUNDEC-4-ENES VIA METALLATED ALLENOL ETHERS. SYNTHESIS OF LACRIMIN A.

Key steps in the first total synthesis of Lacrimin A (2) include (a) the use of methoxyallene as an enone-1,3-dianion equivalent; (b) the use of a new copper-catalysed migratory insertion reaction to construct a tri-substituted alkene stereoselectively; and (c) the use of a Pd(0)-catalysed coupling reaction to generate an isochromanone ring.

A SYNTHESIS OF LACRIMIN A

A convergent synthesis of Lacrimin A (2) is described in which a Wadsworth-Emmons reaction was used to constract the C10-C11 double bond and link the isochroman-1-one phosphonate (4) to the spiroacetal aldehyde (3).