[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane
CAS No.:113453-39-7
Molecular Formula:C₄₂H₆₈O₆Si
Molecular Weight:697.084
Hs Code.:

[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

Synonyms:[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

There total 20 articles about [(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane 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: 94.0%

: 100-39-0
benzyl bromide

: 113453-38-6
<2S,2(4R),5R,6R,7R,8Z,12S>-6,12-dimethyl-13-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-(2,2,4-trimethyl-1,3-dioxolan-4-yl)-7-<(phenylmethoxy)methoxy>-8-tridecen-5-ol

: 113453-39-7
[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With ethanol; potassium hydride; In tetrahydrofuran; at 25 ℃;
DOI:10.1021/ja00216a026

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 113453-39-7
[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / i-Pr₂EtN, Bu₄NI / tetrahydrofuran / 38 h / Ambient temperature

2: 1) O₃, Sudan III indicator, 2) Me₂S / 1) metanol, pyridine, -78 deg C; 2) room temp. 4 h

3: 83 percent / toluene / -78 - -20 deg C, 45 min; 0 deg C, 30 min; 0 deg C - RT, 15 min

4: 97 percent / DIBAL / toluene; tetrahydrofuran / -78 deg C, 30 min; -78 - -50 deg C, 30 min

6: 94 percent / KH, EtOH / tetrahydrofuran / 25 °C

With dimethylsulfide; ethanol; tetra-(n-butyl)ammonium iodide; potassium hydride; diisobutylaluminium hydride; ozone; N-ethyl-N,N-diisopropylamine; Sudan III; In tetrahydrofuran; toluene;
DOI:10.1021/ja00216a026

Reference yield:

: 5673-98-3,63501-27-9,88080-30-2,63501-26-8
(S)-(-)-2-methyl-4-penten-1-ol

: 113453-39-7
[(Z)-(2S,7R,8R,9R,12S)-9-Benzyloxy-7-benzyloxymethoxy-2,8-dimethyl-12-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-tridec-5-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / Et₃N, DMAP / CH₂Cl₂ / 25 °C

2: 1) Cp₂ZrHCl, 2) I₂ / 1) benzene, 25 deg C, 9 h

3: 83 percent / i-Pr₂EtN / acetonitrile / 14 h / 50 °C

4: NaN(SiMe₃)2 / tetrahydrofuran; toluene / 0.25 h / 25 °C

5: 83 percent / toluene / -78 - -20 deg C, 45 min; 0 deg C, 30 min; 0 deg C - RT, 15 min

6: 97 percent / DIBAL / toluene; tetrahydrofuran / -78 deg C, 30 min; -78 - -50 deg C, 30 min

8: 94 percent / KH, EtOH / tetrahydrofuran / 25 °C

With dmap; Schwartz's reagent; ethanol; iodine; sodium hexamethyldisilazane; potassium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja00216a026