dihydrocompactin

Base Information

• Chemical Name: dihydrocompactin
• CAS No.: 78366-44-6
• Molecular Formula: C₂₃H₃₆O₅
• Molecular Weight: 392.536
• Mol file: 78366-44-6.mol

Synonyms:Butanoicacid, 2-methyl-,1,2,3,4,4a,7,8,8a-octahydro-7-methyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenylester, [1S-[1a(R*),4aa,7b,8b(2S*,4S*),8ab]]-;(+)-Dihydrocompactin; 4a,5-Dihydrocompactin; Dihydrocompactin

Chemical Property of dihydrocompactin

Chemical Property:

• Vapor Pressure: 2.04E-13mmHg at 25°C
• Boiling Point: 529.4°C at 760 mmHg
• Flash Point: 175.2°C
• PSA: 72.83000
• Density: 1.11g/cm³
• LogP: 4.02940

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of dihydrocompactin

There total 90 articles about dihydrocompactin 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: 70.0%

(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-[(R)-3-(2-bromo-acetoxy)-5-oxo-pentyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester (853193-48-3) → (S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-[2-((2R,4S)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester + (+)-dihydrocompactin (78366-44-6)

Guidance literature:

With samarium; 1,2-Diiodoethane; In tetrahydrofuran; at -100 - -80 ℃; for 14h;

DOI:10.1021/ja043506g

Reference yield:

(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester (90344-22-2) → (+)-dihydrocompactin (78366-44-6)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 45 ℃; for 6h; Yield given;

DOI:10.1021/ja00325a017

Reference yield:

(R)-4-But-3-ynyl-2,2-dimethyl-[1,3]dioxane (853193-65-4) → (+)-dihydrocompactin (78366-44-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 68 percent / oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / -78 - 20 °C

3.1: 93 percent / amberlyst 15; water / tetrahydrofuran / 24 h / 20 °C

4.1: 79 percent / imidazole / CH₂Cl₂ / 1.33 h / 20 °C

5.1: 85 percent / H₂; quinoline / Lindlar catalyst / hexane / 0.5 h / 20 °C

6.1: Al(OTf)3; TfOH / CH₂Cl₂ / 72 h / -20 °C

6.2: aq. HCl / tetrahydrofuran / 45 °C

6.3: K₂CO₃ / methanol / 2 h / 20 °C

7.1: 84 percent / pyridine / 3 h / 20 °C

8.1: 96 percent / L-selectride / tetrahydrofuran / -78 - 20 °C

9.1: 88 percent / pyridine / CH₂Cl₂ / 0.5 h / -78 °C

10.1: 96 percent / MgBr₂; 1,2,2,6,6-pentamethylpiperidine / tetrahydrofuran; diethyl ether / 1.5 h / 20 °C

11.1: 85 percent / ZnBr₂; MeOH / CH₂Cl₂ / 4 h / 20 °C

12.1: 88 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

13.1: 70 percent / 1,2-diiodoethane; Sm / tetrahydrofuran / 14 h / -100 - -80 °C

With pyridine; 1,2,2,6,6-pentamethylpiperidine; 1H-imidazole; quinoline; methanol; samarium; aluminium(III) triflate; n-butyllithium; Amberlyst 15; oxalyl dichloride; 1,2-Diiodoethane; trifluorormethanesulfonic acid; water; hydrogen; L-Selectride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; magnesium bromide; zinc dibromide; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: Swern oxidation / 6.1: intermolecular Diels-Alder reaction;

DOI:10.1021/ja043506g

upstream raw materials:

(R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester

3,5-Dihydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-heptanoic acid methyl ester

(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester

(S)-2-Methyl-butyric acid (1S,4aR,7S,8S,8aS)-8-[(R)-3-(2-bromo-acetoxy)-5-oxo-pentyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-yl ester