(3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol

Base Information

• Chemical Name: (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol
• CAS No.: 203630-42-6
• Molecular Formula: C₄₂H₆₈O₆Si
• Molecular Weight: 697.084
• Mol file: 203630-42-6.mol

Synonyms:

Chemical Property of (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol

There total 18 articles about (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-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:

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol (73814-75-2,73814-80-9,73837-43-1,79027-31-9,81520-04-9,81520-05-0,81520-09-4,104320-78-7,115458-81-6,115458-82-7,125873-79-2,125873-80-5,81520-08-3) → (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol (203630-42-6)

Guidance literature:

Multi-step reaction with 18 steps

1: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

2: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

3: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

4: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

5: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

6: MCPBA / CH₂Cl₂ / 1 h / -10 °C

7: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

8: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

9: TBAF / tetrahydrofuran / 1 h / 0 °C

10: 85 percent / 1,2-dichloro-ethane; H₂O; hexane / 6 h / -30 °C

11: PPTS / diethyl ether / 1.5 h

12: H₂ / Rh/Al₂O₃ / ethanol / 5 h

13: i-Bu₂AlH / pentane / 1 h / -100 °C

14: 82 percent / toluene / -78 °C

15: KH, 18-c-6 / tetrahydrofuran / 2 h

16: 2,6-lutidine / CH₂Cl₂ / 16 h

17: 1.) OsO₄, NMO; 2.) Pb(OAc)4 / 1.) H₂O, acetone, t-BuOH, 4 h; 2.) benzene, 1 h

18: toluene / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde (618096-09-6) → (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol (203630-42-6)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

2: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

3: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

4: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

5: MCPBA / CH₂Cl₂ / 1 h / -10 °C

6: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

7: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

8: TBAF / tetrahydrofuran / 1 h / 0 °C

9: 85 percent / 1,2-dichloro-ethane; H₂O; hexane / 6 h / -30 °C

10: PPTS / diethyl ether / 1.5 h

11: H₂ / Rh/Al₂O₃ / ethanol / 5 h

12: i-Bu₂AlH / pentane / 1 h / -100 °C

13: 82 percent / toluene / -78 °C

14: KH, 18-c-6 / tetrahydrofuran / 2 h

15: 2,6-lutidine / CH₂Cl₂ / 16 h

16: 1.) OsO₄, NMO; 2.) Pb(OAc)4 / 1.) H₂O, acetone, t-BuOH, 4 h; 2.) benzene, 1 h

17: toluene / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1016/S0040-4039(97)10782-1

Reference yield:

(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate (155430-43-6) → (3R,4R,5R,6S,9S)-9-[(4S,5S,6S)-6-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-5-methyl-[1,3,2]dioxasilinan-4-yl]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-dec-1-en-4-ol (203630-42-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 95 percent / 1,2-dichloro-ethane; H₂O; hexane / -30 °C

2: DMAP, imidazole / dimethylformamide / 2 h / 40 °C

3: i-Bu₂AlH / hexane; CH₂Cl₂ / 1.5 h / -78 °C

4: MCPBA / CH₂Cl₂ / 1 h / -10 °C

5: (COCl)2/DMSO, Et₃N / CH₂Cl₂ / -78 °C

6: 1.) NaH / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 1.5 h

7: TBAF / tetrahydrofuran / 1 h / 0 °C

8: 85 percent / 1,2-dichloro-ethane; H₂O; hexane / 6 h / -30 °C

9: PPTS / diethyl ether / 1.5 h

10: H₂ / Rh/Al₂O₃ / ethanol / 5 h

11: i-Bu₂AlH / pentane / 1 h / -100 °C

12: 82 percent / toluene / -78 °C

13: KH, 18-c-6 / tetrahydrofuran / 2 h

14: 2,6-lutidine / CH₂Cl₂ / 16 h

15: 1.) OsO₄, NMO; 2.) Pb(OAc)4 / 1.) H₂O, acetone, t-BuOH, 4 h; 2.) benzene, 1 h

16: toluene / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium hydride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Rh/Al₂O₃; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; pentane;

DOI:10.1016/S0040-4039(97)10782-1

upstream raw materials:

(S,S)-diisopropyl tartrate (E)-crotylboronate

(2R,3S,4S)-5-benzyloxy-2,3-epoxy-4-methyl-1-pentanol

(2S,3S)-3-((S)-2-benzyloxy-1-methylethyl)oxirane-2-carbaldehyde

(E)-(4R,5S,6S)-ethyl 7-benzyloxy-4,5-epoxy-6-methyl-2-heptenoate

Downstream raw materials:

(4S,5S,6S)-4-((S)-2-Benzyloxy-1-methyl-ethyl)-2,2-di-tert-butyl-6-[(1S,4S,5S,6R,7R)-6-methoxy-4-(4-methoxy-benzyloxy)-1,5,7-trimethyl-9-triisopropylsilanyloxy-nonyl]-5-methyl-[1,3,2]dioxasilinane