(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

Base Information

Chemical Name:(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide
CAS No.:345994-38-9
Molecular Formula:C₃₄H₄₈O₄Si
Molecular Weight:548.838
Hs Code.:

Synonyms:(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

Suppliers and Price of (9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

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Chemical Property of (9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

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Technology Process of (9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

There total 16 articles about (9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide 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: 51.0%

: 345994-36-7
(9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-t-butyldiphenylsilyloxyoctadeca-10,15-dien-9-olide

: 345994-38-9
(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

Guidance literature:: With hydrogen fluoride; In acetonitrile; at 0 - 20 ℃; for 1h;
DOI:10.1016/S0040-4020(01)00279-4

Reference yield:

: 67320-20-1,83692-41-5,94292-91-8,64722-95-8
1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol

: 345994-38-9
(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

Guidance literature:: Multi-step reaction with 15 steps

1.1: 100 percent / sodium hydride / dimethylformamide; various solvent(s) / 2 h

2.1: 85 percent / HgCl₂; yellow HgO / acetonitrile; H₂O / 0.67 h / 0 °C

3.1: diethyl ether; tetrahydrofuran / 1 h / -78 °C

4.1: 96 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 30 h / 40 °C

5.1: 93 percent / pyridine / 1 h

6.1: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

7.1: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -50 - -10 °C

8.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

9.1: 93 percent / lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1.5 h

10.1: 65 percent / (R)-CBS reagent; BH₃*THF / tetrahydrofuran; toluene / 1.5 h

11.1: 91 percent / LiOH*H₂O / methanol / 12 h / 20 °C

12.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 20 °C

12.2: 63 percent / 4-(dimethylamino)pyridine / toluene; tetrahydrofuran / Heating

13.1: 99 percent / sodium bicarbonate; 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 1 h

14.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

15.1: 51 percent / HF / acetonitrile / 1 h / 0 - 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; borane-THF; (R)-CBS reagent; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Wittig reaction / 9.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/S0040-4020(01)00279-4

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 345994-38-9
(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: 51 percent / HF / acetonitrile / 1 h / 0 - 20 °C

With 1H-imidazole; hydrogen fluoride; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)00279-4