(S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

Base Information

Chemical Name:(S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one
CAS No.:858645-42-8
Molecular Formula:C₅₆H₈₈O₇Si₂
Molecular Weight:929.482
Hs Code.:

(S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

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Chemical Property of (S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

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Technology Process of (S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

There total 18 articles about (S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one 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:

: 858645-39-3
5-{[tert-butyl(diphenyl)silyl]oxy}-6-[(Z)-tetradec-2-enyl]tetrahydro-2H-pyran-2-carbaldehyde

: 837428-22-5
(5S)-3-{(2R,8R)-8-hydroxy-2-[2-(trimethylsilyl)ethoxy]dec-9-yn-1-yl}-5-methylfuran-2(5H)-one

: 858645-42-8
(S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

Guidance literature:: With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 20h;
DOI:10.1021/jo052233k

Reference yield:

: 134341-56-3
meso-(2R,5S)-2,5-bis(tert-butyldiphenylsilyloxy)hexane-1,6-dial

: 858645-42-8
(S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 77 percent / NaHMDS / tetrahydrofuran; toluene / 4 h / -78 °C

2.1: NaBH₄ / tetrahydrofuran; propan-2-ol / 3 h / 0 °C

3.1: DMAP / ethanol; various solvent(s) / 14 h / Heating

4.1: 95 percent / PPh₃; DIAD / toluene / 3 h / 20 °C

5.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

5.2: t-BuOK / toluene / 0.83 h / 0 °C

6.1: t-BuOK / toluene / 0 °C

7.1: DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

7.2: 78 percent / NaHMDS / CH₂Cl₂; toluene; tetrahydrofuran / 12 h / -78 - 0 °C

8.1: 81 percent / Al₂O₃ / hexane / 24 h / 20 °C

9.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

10.1: Zn(OTf)2; (1S,2R)-N-methylephedrine; Et₃N / toluene / 20 h / 20 °C

With dmap; aluminum oxide; lithium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; (1S,2R)-(+)-N-methylephedrine; potassium tert-butylate; sodium hexamethyldisilazane; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; isopropyl alcohol; toluene; 1.1: Horner-Wadsworth-Emmons reaction / 4.1: Mitsunobu reaction / 7.2: Wittig reaction / 9.1: Dess-Martin oxidation;
DOI:10.1021/jo052233k

Reference yield:

: 837428-48-5
(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl (2Z,4R,7S)-4,8-bis{[tert-butyl(diphenyl)silyl]oxy}-8-oxooct-2-enoate

: 858645-42-8
(S)-3-[(2R,8R,11R)-11-[(2R,5R,6R)-5-(tert-Butyl-diphenyl-silanyloxy)-6-((Z)-tetradec-2-enyl)-tetrahydro-pyran-2-yl]-8,11-dihydroxy-2-(2-trimethylsilanyl-ethoxy)-undec-9-ynyl]-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaBH₄ / tetrahydrofuran; propan-2-ol / 3 h / 0 °C

2.1: DMAP / ethanol; various solvent(s) / 14 h / Heating

3.1: 95 percent / PPh₃; DIAD / toluene / 3 h / 20 °C

4.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.2: t-BuOK / toluene / 0.83 h / 0 °C

5.1: t-BuOK / toluene / 0 °C

6.1: DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -78 °C

6.2: 78 percent / NaHMDS / CH₂Cl₂; toluene; tetrahydrofuran / 12 h / -78 - 0 °C

7.1: 81 percent / Al₂O₃ / hexane / 24 h / 20 °C

8.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 °C

9.1: Zn(OTf)2; (1S,2R)-N-methylephedrine; Et₃N / toluene / 20 h / 20 °C

With dmap; aluminum oxide; lithium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; (1S,2R)-(+)-N-methylephedrine; potassium tert-butylate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; hexane; dichloromethane; isopropyl alcohol; toluene; 3.1: Mitsunobu reaction / 6.2: Wittig reaction / 8.1: Dess-Martin oxidation;
DOI:10.1021/jo052233k