(2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

Base Information

Chemical Name:(2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate
CAS No.:127750-74-7
Molecular Formula:C₄₅H₇₀O₇SSi
Molecular Weight:783.198
Hs Code.:

(2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

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Chemical Property of (2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

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Technology Process of (2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

There total 12 articles about (2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate 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:

: 129423-03-6
(R)-(+)-4-(phenylsulfonyl)-2-methyl-1-butanol

: 127750-74-7
(2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

Guidance literature:: Multi-step reaction with 12 steps

1: oxalyl chloride, DMSO / CH₂Cl₂ / 0.5 h / -60 °C

2: 1) Mg / 1) I₂ / 1) THF, room temp.; 2) THF, room temp., 16 h

3: 69 percent / trimethylbenzoic acid / toluene / 4 h / 110 °C

4: DIBAL / toluene / 1 h / -90 °C

5: 1) Mg / 1) I₂ / 1) THF, room temp.; 2) THF, room temp. 16 h

6: 81.3 percent / trimethylbenzoic acid / toluene / 3 h / 110 °C

7: DIBAL / toluene / 1 h / -90 °C

8: 85 percent / diethyl ether / -78 - -40 °C

9: 71.3 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

10: 1) BuLi / THF

11: NaBH₄ / ethanol / 5 h / Ambient temperature

12: BuLi, 1,10-phenanthroline / tetrahydrofuran / 4 h / -78 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; trimethylbenzoic acid; diisobutylaluminium hydride; magnesium; dimethyl sulfoxide; iodine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730203

Reference yield:

: (2S)-2-Methyl-4-(phenylsulfonyl)butanal

: 127750-74-7
(2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

Guidance literature:: Multi-step reaction with 11 steps

1: 1) Mg / 1) I₂ / 1) THF, room temp.; 2) THF, room temp., 16 h

2: 69 percent / trimethylbenzoic acid / toluene / 4 h / 110 °C

3: DIBAL / toluene / 1 h / -90 °C

4: 1) Mg / 1) I₂ / 1) THF, room temp.; 2) THF, room temp. 16 h

5: 81.3 percent / trimethylbenzoic acid / toluene / 3 h / 110 °C

6: DIBAL / toluene / 1 h / -90 °C

7: 85 percent / diethyl ether / -78 - -40 °C

8: 71.3 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

9: 1) BuLi / THF

10: NaBH₄ / ethanol / 5 h / Ambient temperature

11: BuLi, 1,10-phenanthroline / tetrahydrofuran / 4 h / -78 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 1,10-Phenanthroline; trimethylbenzoic acid; diisobutylaluminium hydride; magnesium; iodine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730203

Reference yield:

: 127750-71-4
(3RS,4S)-2,4-Dimethyl-6-(phenylsulfonyl)hex-1-en-3-ol

: 127750-74-7
(2R,4S,5RS,6RS,8S,17RS,9E,13E)-17-<(tert-Butyl)dimethylsilyloxy>-4,8,10,14-tetramethyl-2-(2'-methyl-1',3'-dioxolan-2'-yl)-6-(phenylsulfonyl)octadeca-9,13-dien-5-yl Benzoate

Guidance literature:: Multi-step reaction with 10 steps

1: 69 percent / trimethylbenzoic acid / toluene / 4 h / 110 °C

2: DIBAL / toluene / 1 h / -90 °C

3: 1) Mg / 1) I₂ / 1) THF, room temp.; 2) THF, room temp. 16 h

4: 81.3 percent / trimethylbenzoic acid / toluene / 3 h / 110 °C

5: DIBAL / toluene / 1 h / -90 °C

6: 85 percent / diethyl ether / -78 - -40 °C

7: 71.3 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

8: 1) BuLi / THF

9: NaBH₄ / ethanol / 5 h / Ambient temperature

10: BuLi, 1,10-phenanthroline / tetrahydrofuran / 4 h / -78 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; n-butyllithium; 1,10-Phenanthroline; trimethylbenzoic acid; diisobutylaluminium hydride; magnesium; iodine; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; toluene;
DOI:10.1002/hlca.19900730203