33-Norgorgosta-5,24(28)-dien-3β-ol

Base Information

• Chemical Name: 33-Norgorgosta-5,24(28)-dien-3β-ol
• CAS No.: 55064-62-5
• Molecular Weight: 410.67
• Mol file: 55064-62-5.mol

Synonyms:33-Norgorgosta-5,24(28)-dien-3β-ol

Chemical Property of 33-Norgorgosta-5,24(28)-dien-3β-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 33-Norgorgosta-5,24(28)-dien-3β-ol

There total 38 articles about 33-Norgorgosta-5,24(28)-dien-3β-ol 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:

(20S)-3β-acetoxybisnorchol-5-en-22-al (10211-88-8) → <22R,23S>-22,23-methanato-ergosta-5,24(28)-dien-3β-ol (55064-62-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) Mg / 1.) THF, -18 deg C, 1 h; 2.) THF, -18 deg C, 3 h

2: 12.6 g / pyridine / 1 h / Ambient temperature

3: 1.) N-methylmorpholine oxide, osmium tetroxide; 2.) NaHSO₃ / 1.) THF/t-BuOH/H₂O, r.t., 2 h; 2.) THF/t-BuOH/H₂O, r.t., 1 h

4: 12.1 g / sodium metaperiodate / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

5: t-BuOK / tetrahydrofuran / 0.33 h / 0 °C

6: 1.) Mg / 1.) THF, r.t., 1 h; 2.) THF, -18 deg C, 2 h

7: 2.50 g / pyridinium chlorochromate / CH₂Cl₂ / 2 h / Ambient temperature

8: 1.) n-BuLi / 1.) THF, r.t., 30 min; 2.) THF, r.t., 18 h

With pyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; potassium tert-butylate; sodium hydrogensulfite; magnesium; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water;

DOI:10.1248/cpb.29.406

Reference yield:

(20S)-3β-acetoxybisnorchol-5-en-22-al (10211-88-8) → (3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-{(R)-1-[(1S,2R)-2-(2-methyl-1-methylene-propyl)-cyclopropyl]-ethyl}-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (55064-62-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) n-BuLi / 1.) hexane, THF, r.t., 5 min; 2.) hexane, THF, r.t., 30 min

2: pyridine / 2 h / Ambient temperature

3: 6.2 g / 2N H₂SO₄ / dioxane / 0.5 h / 70 °C

4: benzene / 1.5 h / Heating

5: 2.) water / 1.) benzene, reflux, 45 h; 2.) benzene, reflux, 30 min

6: NaBH₄ / ethanol; tetrahydrofuran / 1 h / 0 °C

7: pyridine / Ambient temperature

8: 1.) N-methylmorpholine oxide, osmium tetroxide; 2.) NaHSO₃ / 1.) THF/t-BuOH/H₂O, r.t. ; 2.) THF/t-BuOH/H₂O, r.t.

9: sodium metaperiodate / tetrahydrofuran; H₂O / Ambient temperature

10: 80 percent / t-BuOK / diethyl ether / Ambient temperature

11: 1.) Mg; 3.) pyridinium chlorochomate / 1.) THF, r.t.; 2.) THF, -18 deg C; 3.) CH₂Cl₂, r.t.

12: 1.) n-BuLi / 1.) THF, r.t.; 2.) THF, r.t.

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; sulfuric acid; potassium tert-butylate; water; sodium hydrogensulfite; magnesium; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; water; benzene;

DOI:10.1248/cpb.29.406

Reference yield:

3β-(Tetrahydropyranyloxy)-22-iodo-23,24-bisnorchol-5-ene (78873-43-5) → (3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-{(R)-1-[(1S,2R)-2-(2-methyl-1-methylene-propyl)-cyclopropyl]-ethyl}-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol (55064-62-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 9.24 g / n-BuLi / hexane; tetrahydrofuran / 1.) -18 deg C, 2 h; 2.) r.t., 24 h

2: HgCl₂ / acetonitrile; H₂O / 2 h / Heating

3: pyridine / 3 h / 70 °C

4: benzene / 1.5 h / Heating

5: 2.) water / 1.) benzene, reflux, 45 h; 2.) benzene, reflux, 30 min

6: NaBH₄ / ethanol; tetrahydrofuran / 1 h / 0 °C

7: pyridine / Ambient temperature

8: 1.) N-methylmorpholine oxide, osmium tetroxide; 2.) NaHSO₃ / 1.) THF/t-BuOH/H₂O, r.t. ; 2.) THF/t-BuOH/H₂O, r.t.

9: sodium metaperiodate / tetrahydrofuran; H₂O / Ambient temperature

10: 80 percent / t-BuOK / diethyl ether / Ambient temperature

11: 1.) Mg; 3.) pyridinium chlorochomate / 1.) THF, r.t.; 2.) THF, -18 deg C; 3.) CH₂Cl₂, r.t.

12: 1.) n-BuLi / 1.) THF, r.t.; 2.) THF, r.t.

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; potassium tert-butylate; water; sodium hydrogensulfite; magnesium; 4-methylmorpholine N-oxide; pyridinium chlorochromate; mercury dichloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; water; acetonitrile; benzene;

DOI:10.1248/cpb.29.406

upstream raw materials:

methyl-triphenylphosphonium iodide

Acetic acid (3S,8S,9S,10R,13R,14S,17R)-17-[(R)-1-((1S,2R)-2-isobutyryl-cyclopropyl)-ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

(20S)-3β-acetoxybisnorchol-5-en-22-al

3β-(Tetrahydropyranyloxy)-22-iodo-23,24-bisnorchol-5-ene

Downstream raw materials:

(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-10-Methoxy-3a,5a-dimethyl-6-{(R)-1-[(1S,2R)-2-(2-methyl-1-methylene-propyl)-cyclopropyl]-ethyl}-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene

3α,5-cyclo-22,23-methanato-24-methylene-6β-methoxy-5α-cholestane

Refernces

• 1、 Sato,Akaiwa,Fujimoto,et al.. "Synthesis of demethylgorgosterol and its stereoisomers". . p. 406 - 415. Retrieved 2007/10/02.