(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-en-1-ol

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-en-1-ol
CAS No.:113453-40-0
Molecular Formula:C₃₆H₅₄O₆
Molecular Weight:582.821
Hs Code.:

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-en-1-ol

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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-en-1-ol

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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-en-1-ol

There total 19 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-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:

: 3587-60-8
Benzyloxymethyl chloride

: 113453-40-0
(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-en-1-ol

Guidance literature:: Multi-step reaction with 7 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

7: 98 percent / n-Bu₄N⁺F^- / tetrahydrofuran / 1.25 h / 25 °C

With dimethylsulfide; ethanol; tetrabutyl ammonium fluoride; 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

: 113453-40-0
(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-en-1-ol

Guidance literature:: Multi-step reaction with 9 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

9: 98 percent / n-Bu₄N⁺F^- / tetrahydrofuran / 1.25 h / 25 °C

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

Reference yield:

: 105859-47-0
(S)-tert-butyldimethyl((2-methylpent-4-en-1-yl)oxy)silane

: 113453-40-0
(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-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

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

2: 83 percent / i-Pr₂EtN / acetonitrile / 14 h / 50 °C

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

4: 83 percent / toluene / -78 - -20 deg C, 45 min; 0 deg C, 30 min; 0 deg C - RT, 15 min

5: 97 percent / DIBAL / toluene; tetrahydrofuran / -78 deg C, 30 min; -78 - -50 deg C, 30 min

7: 94 percent / KH, EtOH / tetrahydrofuran / 25 °C

8: 98 percent / n-Bu₄N⁺F^- / tetrahydrofuran / 1.25 h / 25 °C

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