8-Tridecenoic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13-bis[[(1,1-dimethylethyl) diphenylsilyl]oxy]-11-(methoxymethoxy)-2,4,10,12-tetramethyl-, methyl ester, (2R,3S,4S,5S,7S,8Z,10S,11S,12S)-

Base Information

• Chemical Name: 8-Tridecenoic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13-bis[[(1,1-dimethylethyl) diphenylsilyl]oxy]-11-(methoxymethoxy)-2,4,10,12-tetramethyl-, methyl ester, (2R,3S,4S,5S,7S,8Z,10S,11S,12S)-
• CAS No.: 600715-00-2
• Molecular Formula: C64H102O8Si4
• Molecular Weight: 1111.85

Synonyms:

Chemical Property of 8-Tridecenoic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13-bis[[(1,1-dimethylethyl) diphenylsilyl]oxy]-11-(methoxymethoxy)-2,4,10,12-tetramethyl-, methyl ester, (2R,3S,4S,5S,7S,8Z,10S,11S,12S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-Tridecenoic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13-bis[[(1,1-dimethylethyl) diphenylsilyl]oxy]-11-(methoxymethoxy)-2,4,10,12-tetramethyl-, methyl ester, (2R,3S,4S,5S,7S,8Z,10S,11S,12S)-

There total 21 articles about 8-Tridecenoic acid, 3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-7,13-bis[[(1,1-dimethylethyl) diphenylsilyl]oxy]-11-(methoxymethoxy)-2,4,10,12-tetramethyl-, methyl ester, (2R,3S,4S,5S,7S,8Z,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:

(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal (92817-88-4) → (Z)-(2R,3S,4S,5S,7S,10S,11S,12S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7,13-bis-(tert-butyl-diphenyl-silanyloxy)-11-methoxymethoxy-2,4,10,12-tetramethyl-tridec-8-enoic acid methyl ester (600715-00-2)

Guidance literature:

Multi-step reaction with 22 steps

1: 91 percent / diethyl ether / -78 °C

2: 89 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 °C

3: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

4: Dibal-H / CH₂Cl₂ / -78 °C

5: NaBH₄ / methanol / 0 °C

6: pyridine / 25 °C

7: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

8: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

9: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

10: diethyl ether / -78 °C

11: 93 percent / imidazole / CH₂Cl₂

12: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

13: diethyl ether / -78 °C

14: 85 percent / 2,6-lutidine / -78 °C

15: OsO₄; NMO; NaIO₄ / acetone; H₂O

16: 78 percent / diethyl ether / -78 °C

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

18: Dibal-H / toluene / -80 °C

19: 84 percent / 2,6-lutidine / -20 °C

20: OsO₄; NMO; NaIO₄ / acetone; H₂O / 25 °C

21: NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

22: methanol; benzene

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 9: Swern oxidation / 17: Swern oxidation;

DOI:10.1021/ol034958l

Reference yield:

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (106357-24-8) → (Z)-(2R,3S,4S,5S,7S,10S,11S,12S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7,13-bis-(tert-butyl-diphenyl-silanyloxy)-11-methoxymethoxy-2,4,10,12-tetramethyl-tridec-8-enoic acid methyl ester (600715-00-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 89 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 °C

2: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

3: Dibal-H / CH₂Cl₂ / -78 °C

4: NaBH₄ / methanol / 0 °C

5: pyridine / 25 °C

6: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

7: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

8: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

9: diethyl ether / -78 °C

10: 93 percent / imidazole / CH₂Cl₂

11: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

12: diethyl ether / -78 °C

13: 85 percent / 2,6-lutidine / -78 °C

14: OsO₄; NMO; NaIO₄ / acetone; H₂O

15: 78 percent / diethyl ether / -78 °C

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

17: Dibal-H / toluene / -80 °C

18: 84 percent / 2,6-lutidine / -20 °C

19: OsO₄; NMO; NaIO₄ / acetone; H₂O / 25 °C

20: NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

21: methanol; benzene

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 8: Swern oxidation / 16: Swern oxidation;

DOI:10.1021/ol034958l

Reference yield:

(1S,2S)-1-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-2-methylbut-3-enyl prop-2-enoate (468738-71-8) → (Z)-(2R,3S,4S,5S,7S,10S,11S,12S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7,13-bis-(tert-butyl-diphenyl-silanyloxy)-11-methoxymethoxy-2,4,10,12-tetramethyl-tridec-8-enoic acid methyl ester (600715-00-2)

Guidance literature:

Multi-step reaction with 20 steps

1: 85 percent / Grubbs' catalyst / CH₂Cl₂ / Heating

2: Dibal-H / CH₂Cl₂ / -78 °C

3: NaBH₄ / methanol / 0 °C

4: pyridine / 25 °C

5: (i-Pr)2NEt / CH₂Cl₂ / 25 °C

6: 93 percent / Dibal-H / CH₂Cl₂ / -78 °C

7: 90 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

8: diethyl ether / -78 °C

9: 93 percent / imidazole / CH₂Cl₂

10: 89 percent / OsO₄; NMO; NaIO₄ / acetone; H₂O

11: diethyl ether / -78 °C

12: 85 percent / 2,6-lutidine / -78 °C

13: OsO₄; NMO; NaIO₄ / acetone; H₂O

14: 78 percent / diethyl ether / -78 °C

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

16: Dibal-H / toluene / -80 °C

17: 84 percent / 2,6-lutidine / -20 °C

18: OsO₄; NMO; NaIO₄ / acetone; H₂O / 25 °C

19: NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

20: methanol; benzene

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 7: Swern oxidation / 15: Swern oxidation;

DOI:10.1021/ol034958l

upstream raw materials:

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

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

(5S,6S)-6-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-5-methyl-5,6-dihydro-2H-pyran-2-one

(1S,2S)-1-{(1S)-2-[(tert-butyldiphenylsilyl)oxy]-1-methylethyl}-2-methylbut-3-enyl prop-2-enoate

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