83720-10-9

Basic information

• Product Name: (3R,6R,9R)-9-Ethyl-4β-hydroxy-1,7-dioxaspiro[5.5]undecane-3β-methanol
• Synonyms: (-)-Talaromycin A;(3R,6R,9R)-9-Ethyl-4β-hydroxy-1,7-dioxaspiro[5.5]undecane-3β-methanol;Talaromycin A
• CAS NO: 83720-10-9
• Molecular Formula: C₁₂H₂₂O₄
• Molecular Weight: 230.30068
• Mol File: 83720-10-9.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 397.4°C at 760 mmHg
• Flash Point: 194.1°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 5.77E-08mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: (3R,6R,9R)-9-Ethyl-4β-hydroxy-1,7-dioxaspiro[5.5]undecane-3β-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,6R,9R)-9-Ethyl-4β-hydroxy-1,7-dioxaspiro[5.5]undecane-3β-methanol(83720-10-9)
• EPA Substance Registry System: (3R,6R,9R)-9-Ethyl-4β-hydroxy-1,7-dioxaspiro[5.5]undecane-3β-methanol(83720-10-9)

Safety Data

• Hazardous Substances Data: 83720-10-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H22O4/c1-2-9-3-4-12(15-7-9)5-11(14)10(6-13)8-16-12/h9-11,13-14H,2-8H2,1H3/t9-,10-,11+,12-/m1/s1

Upstream product

• 121363-53-9 (3R*,4S*,5S*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-5-chloro-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 121363-52-8 (3R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 121363-54-0 (3S*,4R*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 118418-90-9 C₁₄H₂₆O₃Si 
• 73805-43-3 4-Ethyl-5-hydroxypentanoic acid lactone 
• 121363-48-2 (3S*,6R*,9R*)- and (3R*,6R*,9R*)-9-ethyl-3-hydroxymethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 121363-50-6 2,2-diethyl-5-(6-ethyl-7-hydroxy-3-oxohex-1-yne)-1,3-dioxane 
• 911807-03-9 2-(4-hydroxy-3-hydroxymethylbut-1-ynyl)-5-ethyl-2-methoxytetrahydropyran 
• 121363-53-9 (3S*,4S*,5S*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-5-chloro-9-ethyl-1,7-dioxaspiro<5.5>undecan-4-ol 
• 121363-52-8 (3S*,6R*,9R*)-3-<(t-butyldimethyl)siloxy>methyl-9-ethyl-1,7-dioxaspiro<5.5>undec-4-ene 
• 83720-10-9 (3R,4S,6R)-9-Ethyl-3-hydroxymethyl-1,7-dioxa-spiro[5.5]undecan-4-ol 
• 83720-10-9 talaromycin C 
• 91703-99-0 2-Ethyl-4-((2R,4aR,7R,8aS)-2-phenyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-yl)-butyric acid ethyl ester 
• 91703-98-9 2-Ethyl-4-((2S,4R,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-pyran-2-yl)-butyric acid ethyl ester 

Downstream Products

• 83720-10-9 talaromycin A 
• 83720-10-9 (-)-talaromycin B 
• 106763-16-0 talaromycin A 12-(3',5'-dinitrobenzoate) 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 83720-10-9 talaromycin C 
• 83720-10-9 talaromycin E 
• 83720-10-9 talaromycin F 
• 83720-10-9 talaromycin B 
• 83720-10-9 talaromycin G 
• 113195-31-6 C₂₆H₂₆N₄O₁₄ 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 106763-16-0 3-(9-ethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecyl)methyl (3',5'-dinitro)benzoate 
• 83780-27-2 (-)-Talaromycin B 

Relevant articles and documents

An Enantioselective Total Synthesis of (-)-Talaromycins A and B

The first enantioselective total synthesis of (-)-talaromycin A and B from a common advanced intermediate is described.

Enantioselective Total Synthesis of the Mycotoxin (-)-Talaromycin B by a Hetero Diels-Alder Reaction

(-)-Talaromycin B was formed in an overall yield of 5 percent in nine steps via a hetero Diels-Alder reaction of the exocyclic vinyl ether 3 and methyl O-benzoyldiformylacetate (4) as the key transformation.The enantiomerically pure vinyl ether 3 was prep

Synthesis of Talaromycins A, B, C, and E

The synthesis of 2,2-diethyl-5-ethynyl-1,3-dioxane (9) is reported in an overall yield of 27percent from diethyl malonate.Addition of 5-ethyl tetrahydropyran-2-one to the lithium anion of (9) gave the hydroxy ketoacetylene (10) which was converted in four steps to the olefinic spiroacetals (19) and (20), which were obtained in a ratio of 2:1.The individual olefinic spiroacetals (19) and (20) gave access to the (+/-)-talomycins A and C, and B and E via a chlorohydration, reductive dechlorination, and deprotection sequence.