1,5-Tridecanediol, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenyl silyl]oxy]-3,9-dimethoxy-4,8,10,12-tetramethyl-, (3R,4S,8S,9S,10S,11S,12S)-

Base Information

• Chemical Name: 1,5-Tridecanediol, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenyl silyl]oxy]-3,9-dimethoxy-4,8,10,12-tetramethyl-, (3R,4S,8S,9S,10S,11S,12S)-
• CAS No.: 603994-20-3
• Molecular Formula: C41H72O6Si2
• Molecular Weight: 717.19
• Mol file: 603994-20-3.mol

Synonyms:

Chemical Property of 1,5-Tridecanediol, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenyl silyl]oxy]-3,9-dimethoxy-4,8,10,12-tetramethyl-, (3R,4S,8S,9S,10S,11S,12S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,5-Tridecanediol, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenyl silyl]oxy]-3,9-dimethoxy-4,8,10,12-tetramethyl-, (3R,4S,8S,9S,10S,11S,12S)-

There total 19 articles about 1,5-Tridecanediol, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-13-[[(1,1-dimethylethyl)diphenyl silyl]oxy]-3,9-dimethoxy-4,8,10,12-tetramethyl-, (3R,4S,8S,9S,10S,11S,12S)- 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: 95.0%

(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) → (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 (603994-20-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;

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-4,8,10,12-tetramethyl-tridecane-1,5-diol (603994-20-3)

Guidance literature:

Multi-step reaction with 11 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

11.1: 95 percent / DDQ; MS / CH₂Cl₂

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 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-4,8,10,12-tetramethyl-tridecane-1,5-diol (603994-20-3)

Guidance literature:

Multi-step reaction with 12 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

12.1: 95 percent / DDQ; MS / CH₂Cl₂

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 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,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

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

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

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester