(5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene

Base Information

• Chemical Name: (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene
• CAS No.: 338956-92-6
• Molecular Formula: C₄₁H₇₈O₄Si₃
• Molecular Weight: 719.324
• Mol file: 338956-92-6.mol

Synonyms:(5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene

Chemical Property of (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene

There total 26 articles about (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10⁽¹⁹⁾-triene 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: 33.0%

(1S,3aR,7aR)-1-[(S)-1-(3-methyl-3-trimethylsilyloxybutyloxy)ethyl]-7a-methyloctahydro-1H-inden-4-one (192573-33-4) + (Z,3R,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylideneethyl]diphenylphosphine oxide (338956-85-7) → (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10(19)-triene (338956-92-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 5h;

DOI:10.1016/S0968-0896(00)00259-5

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10(19)-triene (338956-92-6)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 21 h / 20 °C

2.1: DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

2.2: 81 percent / NaBH₄ / methanol / 0.5 h / 20 °C

3.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -63 - 20 °C

4.1: 86 percent / NaH / tetrahydrofuran / 0.5 h / -78 °C

5.1: 87 percent / DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

6.1: 100 percent / D-DIPT; Ti(OiPr)4; t-BuOOH / CH₂Cl₂ / -30 - -15 °C

7.1: 70 percent / Red-Al / toluene / 21 h / -30 °C

8.1: 95 percent / pyridine / CH₂Cl₂ / 3.5 h / 20 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 80 percent / aq. NaOH / methanol / 11 h / 20 °C

11.1: 1.97 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

12.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

13.1: 69 percent / Dess-Martin reagent / CH₂Cl₂ / 15 h / 20 °C

14.1: 85 percent / NaH / tetrahydrofuran / -5 - 20 °C

15.1: 98 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

16.1: 52 percent / Ph₃P; Et₃N; Pd(OAc)2 / dimethylformamide / 24.5 h / 20 °C

17.1: 83 percent / N-chlorosuccinimide; DMS / CH₂Cl₂ / 1 h / 20 °C

18.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -50 °C

18.2: 86 percent / aq. H₂O₂ / CHCl₃; tetrahydrofuran / 0.5 h / 20 °C

19.1: 33 percent / n-BuLi / tetrahydrofuran; hexane / 5 h / -78 °C

With pyridine; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; palladium diacetate; sodium hydroxide; N-chloro-succinimide; n-butyllithium; oxalyl dichloride; 2,3-dimercapto-succinic acid; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.2: reduction / 3.1: Swern oxidation / 4.1: Horner-Emmons reaction / 6.1: Katsuki-Sharpless epoxidation / 11.1: Swern oxidation / 13.1: Dess-Martin oxidation / 16.1: Heck reaction / 18.2: oxidation;

DOI:10.1016/S0968-0896(00)00259-5

Reference yield:

(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol (158817-21-1) → (5Z,7E,1R,3S,20S)-1,3-bis(tert-butyldimethylsilyloxy)-20-(3-methyl-3-trimethylsilyloxybutyloxy)-9,10-secopregna-5,7,10(19)-triene (338956-92-6)

Guidance literature:

Multi-step reaction with 22 steps

1.1: D-DIPT; Ti(OiPr)4; t-BuOOH / CH₂Cl₂ / -25 - -15 °C

2.1: 99 percent / imidazole; Ph₃P; I₂ / tetrahydrofuran; acetonitrile / 0.5 h / 20 °C

3.1: 98 percent / Zn; AcOH / methanol / 2.5 h / 37 °C

4.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 21 h / 20 °C

5.1: DDQ / CH₂Cl₂; H₂O / 1 h / 0 °C

5.2: 81 percent / NaBH₄ / methanol / 0.5 h / 20 °C

6.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -63 - 20 °C

7.1: 86 percent / NaH / tetrahydrofuran / 0.5 h / -78 °C

8.1: 87 percent / DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

9.1: 100 percent / D-DIPT; Ti(OiPr)4; t-BuOOH / CH₂Cl₂ / -30 - -15 °C

10.1: 70 percent / Red-Al / toluene / 21 h / -30 °C

11.1: 95 percent / pyridine / CH₂Cl₂ / 3.5 h / 20 °C

12.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 80 percent / aq. NaOH / methanol / 11 h / 20 °C

14.1: 1.97 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

15.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

16.1: 69 percent / Dess-Martin reagent / CH₂Cl₂ / 15 h / 20 °C

17.1: 85 percent / NaH / tetrahydrofuran / -5 - 20 °C

18.1: 98 percent / DIBAL / CH₂Cl₂; toluene / 0.5 h / -78 °C

19.1: 52 percent / Ph₃P; Et₃N; Pd(OAc)2 / dimethylformamide / 24.5 h / 20 °C

20.1: 83 percent / N-chlorosuccinimide; DMS / CH₂Cl₂ / 1 h / 20 °C

21.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -50 °C

21.2: 86 percent / aq. H₂O₂ / CHCl₃; tetrahydrofuran / 0.5 h / 20 °C

22.1: 33 percent / n-BuLi / tetrahydrofuran; hexane / 5 h / -78 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; palladium diacetate; sodium hydroxide; N-chloro-succinimide; n-butyllithium; oxalyl dichloride; 2,3-dimercapto-succinic acid; iodine; sodium hydride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Katsuki-Sharpless epoxidation / 5.2: reduction / 6.1: Swern oxidation / 7.1: Horner-Emmons reaction / 9.1: Katsuki-Sharpless epoxidation / 14.1: Swern oxidation / 16.1: Dess-Martin oxidation / 19.1: Heck reaction / 21.2: oxidation;

DOI:10.1016/S0968-0896(00)00259-5

upstream raw materials:

(1S,3aR,7aR)-1-[(S)-1-(3-methyl-3-trimethylsilyloxybutyloxy)ethyl]-7a-methyloctahydro-1H-inden-4-one

(Z,3R,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylideneethyl]diphenylphosphine oxide

tert-butyldimethylsilyl chloride

maxacalcitol

Refernces