(-)-4,4,8-Trimethyl-18-nor-15-oxa-5α-androsta-13,16-diene-19-oic acid

Base Information

Chemical Name:(-)-4,4,8-Trimethyl-18-nor-15-oxa-5α-androsta-13,16-diene-19-oic acid
CAS No.:97640-44-3
Molecular Formula:C₂₀H₂₈O₃
Molecular Weight:316.441
Hs Code.:
Mol file:97640-44-3.mol

Synonyms:marginatafuran;isospongia-13,15-dien-20-oic acid;(3bR,5aS,9aR,9bS)-3b,6,6-Trimethyl-3b,5,5a,6,7,8,9,9b,10,11-decahydro-4H-phenanthro[1,2-b]furan-9a-carboxylic acid;

Suppliers and Price of (-)-4,4,8-Trimethyl-18-nor-15-oxa-5α-androsta-13,16-diene-19-oic acid

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (-)-4,4,8-Trimethyl-18-nor-15-oxa-5α-androsta-13,16-diene-19-oic acid

Chemical Property:

PSA：50.44000
LogP:4.79080

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (-)-4,4,8-Trimethyl-18-nor-15-oxa-5α-androsta-13,16-diene-19-oic acid

There total 21 articles about (-)-4,4,8-Trimethyl-18-nor-15-oxa-5α-androsta-13,16-diene-19-oic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

: 1382088-01-8
methyl 3,12-dioxoisospongia-13,15-dien-20-oate

: 97640-44-3
isospongia-13,15-dien-20-oic acid

Guidance literature:: methyl 3,12-dioxoisospongia-13,15-dien-20-oate; With hydrazine; In diethylene glycol; at 120 - 170 ℃; for 1.5h; Inert atmosphere;

With potassium hydroxide; In diethylene glycol; at 185 ℃; for 8h; Inert atmosphere;

With hydrogenchloride; In water; diethylene glycol; diastereoselective reaction;
DOI:10.1021/jo3008034

Reference yield:

: 1382087-86-6
(1S,3R,4S,6S)-4-(3-chloroprop-1-en-2-yl)-3-(3,3-diethoxypropyl)-1,3-dimethyl-7-oxabicyclo[4.1.0]heptan-2-one

: 97640-44-3
isospongia-13,15-dien-20-oic acid

Guidance literature:: Multi-step reaction with 17 steps

1.1: N-ethylmorpholine N-oxide; lithium iodide / N,N-dimethyl-formamide / 30 h / 55 °C

2.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 0 °C

3.1: 0 °C

4.1: pyridinium p-toluenesulfonate / acetone / 45 °C

5.1: dichloromethane / 36 h / 28 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / -78 °C

7.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene; methyloxirane / 96 h / 140 °C / Inert atmosphere

8.1: diethylzinc / hexane; toluene / 4 h / 0 °C

9.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / -30 - 20 °C

10.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 0 °C

11.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; diethylaluminium chloride / hexane; toluene / 1.33 h / 0 °C

12.1: Grubbs catalyst first generation; p-benzoquinone / dichloromethane / 1 h / Reflux

13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 20 °C / Inert atmosphere

14.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Molecular sieve

15.1: fluorosilicic acid / water; acetonitrile / 18 h / 0 - 4 °C

16.1: sodium hydroxide / 1,4-dioxane; water / 6 h / 90 °C / Inert atmosphere

17.1: hydrazine / diethylene glycol / 1.5 h / 120 - 170 °C / Inert atmosphere

17.2: 8 h / 185 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; Grubbs catalyst first generation; sodium chlorite; sodium tetrahydroborate; n-butyllithium; N-ethylmorpholine N-oxide; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; cerium(III) chloride heptahydrate; 2,6-di-tert-butyl-4-methyl-phenol; fluorosilicic acid; diethylzinc; diethylaluminium chloride; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; sodium hydroxide; lithium iodide; hydrazine; In 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; methyloxirane; mineral oil; tert-butyl alcohol; diethylene glycol; benzene;
DOI:10.1021/jo3008034

Reference yield:

: 1382087-87-7
2-((1S,3R,4R,6S)-4-(3,3-diethoxypropyl)-4,6-dimethyl-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl)acrylaldehyde

: 97640-44-3
isospongia-13,15-dien-20-oic acid

Guidance literature:: Multi-step reaction with 16 steps

1.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 0 °C

2.1: 0 °C

3.1: pyridinium p-toluenesulfonate / acetone / 45 °C

4.1: dichloromethane / 36 h / 28 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / -78 °C

6.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene; methyloxirane / 96 h / 140 °C / Inert atmosphere

7.1: diethylzinc / hexane; toluene / 4 h / 0 °C

8.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol; dichloromethane / -30 - 20 °C

9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 0 °C

10.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium; diethylaluminium chloride / hexane; toluene / 1.33 h / 0 °C

11.1: Grubbs catalyst first generation; p-benzoquinone / dichloromethane / 1 h / Reflux

12.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 20 °C / Inert atmosphere

13.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / Molecular sieve

14.1: fluorosilicic acid / water; acetonitrile / 18 h / 0 - 4 °C

15.1: sodium hydroxide / 1,4-dioxane; water / 6 h / 90 °C / Inert atmosphere

16.1: hydrazine / diethylene glycol / 1.5 h / 120 - 170 °C / Inert atmosphere

16.2: 8 h / 185 °C / Inert atmosphere

With 2,2,6,6-tetramethyl-piperidine; Grubbs catalyst first generation; sodium chlorite; sodium tetrahydroborate; n-butyllithium; tetrapropylammonium perruthennate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; cerium(III) chloride heptahydrate; 2,6-di-tert-butyl-4-methyl-phenol; fluorosilicic acid; diethylzinc; diethylaluminium chloride; pyridinium p-toluenesulfonate; sodium hydride; 4-methylmorpholine N-oxide; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; p-benzoquinone; sodium hydroxide; hydrazine; In 1,4-dioxane; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; methyloxirane; mineral oil; tert-butyl alcohol; diethylene glycol; benzene;
DOI:10.1021/jo3008034