7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane

Base Information

• Chemical Name: 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane
• CAS No.: 166896-86-2
• Molecular Formula: C₅₇H₁₀₁N₃O₆Si
• Molecular Weight: 952.531

Synonyms:7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane

Chemical Property of 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane

There total 15 articles about 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane 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:

3β-hydroxy-5-cholenoic acid (5255-17-4) → 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane (166896-86-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 92 percent / PPTS / CH₂Cl₂ / Ambient temperature

2: 92 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3: 98 percent / imidazole / CH₂Cl₂ / Ambient temperature

4: 59 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / Ambient temperature

5: 71 percent / H₂ / PtO₂ / ethyl acetate / 2.5 h

6: 94 percent / K-Selectride / tetrahydrofuran / 5 h / 50 °C

7: 87 percent / NaH / dimethylformamide; tetrahydrofuran / 1.) overnight; 40 deg C, 20 min, 2.) 40 deg C, 10 h

8: 90 percent / TBAF / tetrahydrofuran

9: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 40 min, 2.) 0 deg C, 30 min

10: 77 percent / tetrahydrofuran / Ambient temperature

11: 96 percent / imidazole / CH₂Cl₂ / 24 h / Ambient temperature

12: 98 percent / MgBr₂ / diethyl ether

13: 87 percent / Collin's reagent / CH₂Cl₂ / Ambient temperature

14: 1.) molecular sieves 3 Angstroem, 2.) NaCNBH₃ / 1.) MeOH, r.t., 12 h, 2.) THF, r.t., 24 h

With 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; lithium aluminium tetrahydride; oxalyl dichloride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; dipyridine chromium trioxide; sodium hydride; sodium cyanoborohydride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a033

Reference yield:

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol (66414-43-5) → 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane (166896-86-2)

Guidance literature:

Multi-step reaction with 12 steps

1: 98 percent / imidazole / CH₂Cl₂ / Ambient temperature

2: 59 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / Ambient temperature

3: 71 percent / H₂ / PtO₂ / ethyl acetate / 2.5 h

4: 94 percent / K-Selectride / tetrahydrofuran / 5 h / 50 °C

5: 87 percent / NaH / dimethylformamide; tetrahydrofuran / 1.) overnight; 40 deg C, 20 min, 2.) 40 deg C, 10 h

6: 90 percent / TBAF / tetrahydrofuran

7: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 40 min, 2.) 0 deg C, 30 min

8: 77 percent / tetrahydrofuran / Ambient temperature

9: 96 percent / imidazole / CH₂Cl₂ / 24 h / Ambient temperature

10: 98 percent / MgBr₂ / diethyl ether

11: 87 percent / Collin's reagent / CH₂Cl₂ / Ambient temperature

12: 1.) molecular sieves 3 Angstroem, 2.) NaCNBH₃ / 1.) MeOH, r.t., 12 h, 2.) THF, r.t., 24 h

With 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; oxalyl dichloride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dipyridine chromium trioxide; sodium hydride; sodium cyanoborohydride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a033

Reference yield:

24-<(tert-Butyldimethylsilyl)oxy>-3β-(tetrahydropyranyloxy)chol-5-ene (166896-75-9) → 7α-(Benzyloxy)-3ξ-<5,10-bis(tert-butoxycarbonyl)-1,5,10-triazadecyl>-24ξ-<(tert-butyldimethylsilyl)oxy>-cholestane (166896-86-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 59 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / Ambient temperature

2: 71 percent / H₂ / PtO₂ / ethyl acetate / 2.5 h

3: 94 percent / K-Selectride / tetrahydrofuran / 5 h / 50 °C

4: 87 percent / NaH / dimethylformamide; tetrahydrofuran / 1.) overnight; 40 deg C, 20 min, 2.) 40 deg C, 10 h

5: 90 percent / TBAF / tetrahydrofuran

6: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 40 min, 2.) 0 deg C, 30 min

7: 77 percent / tetrahydrofuran / Ambient temperature

8: 96 percent / imidazole / CH₂Cl₂ / 24 h / Ambient temperature

9: 98 percent / MgBr₂ / diethyl ether

10: 87 percent / Collin's reagent / CH₂Cl₂ / Ambient temperature

11: 1.) molecular sieves 3 Angstroem, 2.) NaCNBH₃ / 1.) MeOH, r.t., 12 h, 2.) THF, r.t., 24 h

With 1H-imidazole; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; oxalyl dichloride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dipyridine chromium trioxide; sodium hydride; sodium cyanoborohydride; potassium tri-sec-butyl-borohydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00121a033

upstream raw materials:

N₁,N₅-di-boc-spermidine

7α-(Benzyloxy)-24ξ-<(tert-butyldimethylsilyl)oxy>cholest-3-one

3β-hydroxy-5-cholenoic acid

3β-(tetrahydro-2H-pyran-2-yloxy)chol-5-en-24-ol

Downstream raw materials:

7α-(Benzyloxy)-3β-(1,5,10-triazadecyl)cholestan-24ξ-ol

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