(3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol

Base Information

• Chemical Name: (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol
• CAS No.: 603994-19-0
• Molecular Formula: C₄₉H₈₀O₇Si₂
• Molecular Weight: 837.341

Synonyms:(3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol

Chemical Property of (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol

There total 21 articles about (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-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: 90.0%

(3R,4R,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-one (603994-18-9) → (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol (603994-19-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃; for 1h;

DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol (603994-19-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

1.2: 98 percent / CH₂Cl₂ / 2 h / -78 - -10 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 75 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: tert-BuOK; n-BuLi; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / -78 - -45 °C

5.2: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

5.3: 220 mg / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane / 25 °C

6.1: 78 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 14 h / 0 - 20 °C

7.1: OsO₄; NMO; H₂O / acetone / 20 °C

7.2: HIO₆; H₂O / acetone / 0.5 h

8.1: activated Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

8.2: 76 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

9.1: 90 percent / H₂ / Pt/C / ethanol / 2 h

10.1: 90 percent / NaBH₄ / methanol / 1 h / 20 °C

With (+)-Ipc₂BOMe; 2,6-dimethylpyridine; barium dihydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; water; hydrogen; dimethyl sulfoxide; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetone; 4.1: Swern oxidation / 8.2: Wadsworth-Emmons coupling;

DOI:10.1016/S0957-4166(03)00372-0

Reference yield:

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol (95514-04-8) → (3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-ol (603994-19-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

2.2: 98 percent / CH₂Cl₂ / 2 h / -78 - -10 °C

3.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 75 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: tert-BuOK; n-BuLi; (+)-B-methoxydiisopinocampheylborane / tetrahydrofuran; hexane / -78 - -45 °C

6.2: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

6.3: 220 mg / aq. NaOH; H₂O₂ / tetrahydrofuran; hexane / 25 °C

7.1: 78 percent / 2,6-di-tert-butylpyridine / CH₂Cl₂ / 14 h / 0 - 20 °C

8.1: OsO₄; NMO; H₂O / acetone / 20 °C

8.2: HIO₆; H₂O / acetone / 0.5 h

9.1: activated Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

9.2: 76 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

10.1: 90 percent / H₂ / Pt/C / ethanol / 2 h

11.1: 90 percent / NaBH₄ / methanol / 1 h / 20 °C

With (+)-Ipc₂BOMe; 2,6-dimethylpyridine; barium dihydroxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; water; hydrogen; dimethyl sulfoxide; triethylamine; platinum on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetone; 1.1: Swern oxidation / 5.1: Swern oxidation / 9.2: Wadsworth-Emmons coupling;

DOI:10.1016/S0957-4166(03)00372-0

upstream raw materials:

(3R,4R,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-1-(4-methoxy-benzyloxy)-4,8,10,12-tetramethyl-tridecan-5-one

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

3-(p-methoxybenzyloxy)propanal

(R)-3-(tert-butyldiphenylsilyloxy)-2-methylpropan-1-ol

Downstream raw materials:

(3R,4S,8S,9S,10S,11S,12S)-11-(tert-Butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-3,9-dimethoxy-4,8,10,12-tetramethyl-tridecane-1,5-diol

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