(1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol

Base Information

Chemical Name:(1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol
CAS No.:287483-51-6
Molecular Formula:C₃₅H₅₄O₃Si
Molecular Weight:550.897
Hs Code.:

Synonyms:(1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol

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Chemical Property of (1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol

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Technology Process of (1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol

There total 28 articles about (1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-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:

: 165605-79-8
(4S,5S)-4,5-dihydro-4-hydroxy-5-pentyl-2-(3H)-furanone

: 287483-51-6
(1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

2: DIBAL-H / diethyl ether; cyclohexane / -78 °C

3: 18.5 g / benzene / 2 h / 50 °C

4: 77 percent / DIBAL-H / diethyl ether; cyclohexane / 0 °C

5: 82 percent / Ti(OPr-i)4; (S,S)-(-)-DET; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

6: Et₃N / CH₂Cl₂ / 2 h / 0 °C

7: 1.56 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

8: 80 percent / NaH; MeOH / CH₂Cl₂ / 0 - 20 °C

9: CuI / tetrahydrofuran / -30 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; cyclohexane; benzene; 3: Wittig olefination / 5: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/jo0057194

Reference yield:

: 287483-41-4
(4S,5S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyldihydrofuran-2-one

: 287483-51-6
(1S)-1-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-dec-9-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: DIBAL-H / diethyl ether; cyclohexane / -78 °C

2: 18.5 g / benzene / 2 h / 50 °C

3: 77 percent / DIBAL-H / diethyl ether; cyclohexane / 0 °C

4: 82 percent / Ti(OPr-i)4; (S,S)-(-)-DET; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

5: Et₃N / CH₂Cl₂ / 2 h / 0 °C

6: 1.56 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

7: 80 percent / NaH; MeOH / CH₂Cl₂ / 0 - 20 °C

8: CuI / tetrahydrofuran / -30 °C

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; copper(l) iodide; diethyl (2S,3S)-tartrate; sodium hydride; diisobutylaluminium hydride; triethylamine; 4 A molecular sieve; In tetrahydrofuran; 2,2,4-trimethylpentane; diethyl ether; dichloromethane; cyclohexane; benzene; 2: Wittig olefination / 4: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/jo0057194