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
• Article Data: 5

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

• 121741-37-5 9-{(2S,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-eth-(E)-ylidene]-2-methyl-oxepan-2-yl}-2,6-dimethyl-non-2-en-5-ol 
• 100582-59-0 (2SR,3RS,6E)-3-t-butyldimethylsiloxy-(2-t-butyldimethylsiloxyethilidene)-2-(4,8-dimethyl-5-oxo-non-7-enyl)-2-methyloxepane 
• 2468-55-5 5-iodopent-1-yne 
• 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 

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.

TOTAL SYNTHESIS OF (+/-) ZOAPATANOL

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

Total Synthesis of (+/-)-Zoapatanol

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