(3S,3aS,6aS,10S,10aR)-3,10-dihydroxy-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-4-carbaldehyde

Base Information

• Chemical Name: (3S,3aS,6aS,10S,10aR)-3,10-dihydroxy-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-4-carbaldehyde
• CAS No.: 158761-03-6
• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.321
• Mol file: 158761-03-6.mol

Synonyms:1H-Naphtho[1,8a-c]furan-4-carboxaldehyde,3,3a,6,6a,7,8,9,10-octahydro-3,10-dihydroxy-7,7-dimethyl-1-oxo-, [3S-(3a,3aa,6aa,10a,10aS*)]-; (-)-Mniopetal F;Mniopetal F

Chemical Property of (3S,3aS,6aS,10S,10aR)-3,10-dihydroxy-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-4-carbaldehyde

Chemical Property:

• Vapor Pressure: 3.67E-13mmHg at 25°C
• Boiling Point: 523.8°Cat760mmHg
• Flash Point: 198.5°C
• Density: 1.32g/cm³

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3S,3aS,6aS,10S,10aR)-3,10-dihydroxy-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-4-carbaldehyde

There total 21 articles about (3S,3aS,6aS,10S,10aR)-3,10-dihydroxy-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydronaphtho[1,8a-c]furan-4-carbaldehyde 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: 100.0%

(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde (330998-95-3) → mniopetal F (158761-03-6)

Guidance literature:

In water; acetone; trifluoroacetic acid; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200102)2001:3<473::AID-EJOC473>3.0.CO;2-J

Reference yield: 83.0%

(1R,2S,6S,9S,10S,12R,15S)-10-methoxy-2-(methoxymethoxy)-5,5-dimethyl-11,13-dioxatetracyclo[10.2.1.01,6.09,15]pentadec-7-en-14-one (374570-67-9) → mniopetal F (158761-03-6)

Guidance literature:

(1R,2S,6S,9S,10S,12R,15S)-10-methoxy-2-(methoxymethoxy)-5,5-dimethyl-11,13-dioxatetracyclo[10.2.1.0^1,6.0^9,15]pentadec-7-en-14-one; With hydrogenchloride; In tetrahydrofuran; for 44h;

With triethylamine; In toluene; for 20h;

DOI:10.1016/S0040-4020(01)00686-X

Reference yield:

2-hydroxy-5,5-dimethyl-9-(1,3-dithiolan-2-yl)-12-oxatricyclo[8.3.0.01,6]tridec-7-en-11-one → mniopetal F (158761-03-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 44 percent / CaCO₃; Hg(ClO₄)2*3H₂O / methanol; CHCl₃ / 20 h / 0 °C

2.1: 85 percent / DIPEA / CH₂Cl₂ / 19 h / 40 °C

3.1: 100 percent / aq. KOH; aq. NaOH; Na₂RuO₄ / 2-methyl-propan-2-ol / 14 h / 80 °C

4.1: 44 percent / DIBALH / toluene / 0.42 h / -78 °C

5.1: 43 percent / p-toluenesulfonic acid monohydrate / tetrahydrofuran; H₂O / 2.5 h / 0 °C

6.1: 80 percent / DMSO; Ac₂O / 6 h

7.1: aq. HCl / tetrahydrofuran / 44 h

7.2: 83 percent / Et₃N / toluene / 20 h

With hydrogenchloride; potassium hydroxide; sodium hydroxide; mercury(II) perchlorate; sodium ruthenate(VI); acetic anhydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; toluene; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)00686-X

upstream raw materials:

(3S,3aS,6aS,10S,10aR)-10-Hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-1-oxo-3,3a,6,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalene-4-carbaldehyde

(1R,2S,6S,9S,10S,12R,15S)-10-methoxy-2-(methoxymethoxy)-5,5-dimethyl-11,13-dioxatetracyclo[10.2.1.0^1,6.0^9,15]pentadec-7-en-14-one

(1S,2S,6S,9S,10S)-2-hydroxy-9-(dimethoxy)methyl-5,5-dimethyl-12-oxatricyclo[8.3.0.0^1,6]tridec-7-en-11-one

(1R,2S,6S,9S,10S,12S,15S)-10-methoxy-2-(methoxymethoxy)-5,5-dimethyl-11,13-dioxatetracyclo[10.2.1.0^1,6.0^9,15]pentadec-7-en-14-ol