71117-51-6

Basic information

• Product Name: (+)-Zoapatanol
• Synonyms: (+)-Zoapatanol;(R)-9-[(2S,3R,6E)-3α-Hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2β-yl]-2,6-dimethyl-2-nonen-5-one;(R)-9-[(2S,6E)-3α-Hydroxy-6-(2-hydroxyethylidene)-2-methyloxepan-2β-yl]-2,6-dimethyl-2-nonen-5-one;Zoapatanol
• CAS NO: 71117-51-6
• Molecular Formula: C20H34O4
• Molecular Weight: 0
• Mol File: 71117-51-6.mol

Chemical Properties

• Boiling Point: 489.2°C at 760 mmHg
• Flash Point: 164°C
• Appearance: /
• Density: 1.049g/cm³
• Vapor Pressure: 1.27E-11mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: (+)-Zoapatanol(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Zoapatanol(71117-51-6)
• EPA Substance Registry System: (+)-Zoapatanol(71117-51-6)

Safety Data

• Hazardous Substances Data: 71117-51-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H34O4/c1-15(2)7-9-18(22)16(3)6-5-12-20(4)19(23)10-8-17(11-13-21)14-24-20/h7,11,16,19,21,23H,5-6,8-10,12-14H2,1-4H3/b17-11+/t16-,19-,20+/m1/s1

Upstream product

• 67441-39-8 Acetic acid (2S,3R)-6-[2-acetoxy-eth-(Z)-ylidene]-2-(4,8-dimethyl-5-oxo-non-7-enyl)-2-methyl-oxepan-3-yl ester 
• 20038-12-4 4-bromo-2-methylbut-1-ene 
• 73617-77-3 Acetic acid (2S,3R)-2-(5-hydroxy-4,8-dimethyl-non-7-enyl)-2-methyl-6-oxo-oxepan-3-yl ester 
• 73617-69-3 5-((8S,9R)-9-Benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-2-methyl-pentanal 
• 73617-66-0 5-((8S,9R)-9-Benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-2-methyl-pentan-1-ol 
• 73617-75-1 (8R,9S)-8-[4,8-Dimethyl-5-(tetrahydro-pyran-2-yloxy)-non-7-enyl]-8-methyl-1,4,7-trioxa-spiro[4.6]undecan-9-ol 
• 77513-81-6 (6R,7S)-6-Benzyloxy-7-methyl-7-[4-methyl-5-(tetrahydro-pyran-2-yloxy)-pentyl]-oxepan-3-one 
• 73617-73-9 9-((8S,9R)-9-Benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-2,6-dimethyl-non-2-en-5-ol 
• 73617-70-6 9-((8S,9R)-9-Benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-2,6-dimethyl-non-1-en-5-ol 
• 73617-78-4 Acetic acid (2S,3R)-2-[4,8-dimethyl-5-(tetrahydro-pyran-2-yloxy)-non-7-enyl]-2-methyl-6-oxo-oxepan-3-yl ester 
• 73617-76-2 Acetic acid (8S,9R)-8-[4,8-dimethyl-5-(tetrahydro-pyran-2-yloxy)-non-7-enyl]-8-methyl-1,4,7-trioxa-spiro[4.6]undec-9-yl ester 
• 73617-72-8 Acetic acid 1-[4-((8S,9R)-9-benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-1-methyl-butyl]-4-methyl-pent-3-enyl ester 
• 73617-71-7 Acetic acid 1-[4-((8S,9R)-9-benzyloxy-8-methyl-1,4,7-trioxa-spiro[4.6]undec-8-yl)-1-methyl-butyl]-4-methyl-pent-4-enyl ester 
• 73617-79-5 [(6R,7S)-6-Acetoxy-7-[4,8-dimethyl-5-(tetrahydro-pyran-2-yloxy)-non-7-enyl]-7-methyl-oxepan-(3Z)-ylidene]-acetic acid ethyl ester 

Relevant articles and documents

A SYNTHESIS OF ZOAPATANOL

Organomagnesium chemistry plays a crusial role in the stereoselective construction of the two tri-substituted alkenes in the diol (3)-a key intermediate in a synthesis of the spasmogenic diterpenoid zoapatanol (1).A Ni(0)-catalysed coupling of MeMgBr with a dihydrofuran gives the C(6)-C(7) alkene; carbomagnesiation or hydromagnesiation of acetylene intermediates gives the C(2)-C(3) alkene.

A Total Synthesis of Zoapatanol

A key step in a new synthesis of zoapatanol involves stannic chloride catalysed isomerisation of the epoxy diol (21) to the oxepane (22) with inversion of configuration of the tertiary carbon atom.Differential protection of the hydroxy groups allows oxida

TOTAL SYNTHESIS OF (+/-) ZOAPATANOL

A stereoselective synthesis of (+/-) zoapatanol is described.