(3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

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Chemical Name:(3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol
CAS No.:1335101-38-6
Molecular Formula:C₃₈H₅₆O₅
Molecular Weight:592.86
Hs Code.:

Synonyms:(3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

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Chemical Property of (3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

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Technology Process of (3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

There total 20 articles about (3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-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: 70.0%

: 1335101-51-3
(3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-((S)-1-((R)-oxiran-2-yl)undecyloxy)deca-1,9-dien-3-ol

: 2181-42-2
trimethylsulphonium iodide

: 1335101-38-6
(3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

Guidance literature:: trimethylsulphonium iodide; With n-butyllithium; In tetrahydrofuran; hexanes; at -10 ℃; for 1h; Inert atmosphere;

(3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-((S)-1-((R)-oxiran-2-yl)undecyloxy)deca-1,9-dien-3-ol; In tetrahydrofuran; hexanes; at -10 - 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tet.2011.07.079

Reference yield:

: 1335101-40-0
(S,3E,5E)-1-((S)-p-tolylsulfinyl)hepta-3,5-dien-2-ol

: 1335101-38-6
(3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: water / toluene / 0.08 h / 20 °C

2.2: 2 h / 20 °C

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / dichloromethane / 4 h / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 96 h / Inert atmosphere; Reflux

6.1: platinum oxide on carbon; hydrogen / methanol; benzene / 24 h / 20 °C / 7500.75 Torr / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

8.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere

10.1: ethanol; magnesium; mercury dichloride / 4 h / 0 - 20 °C / Inert atmosphere

11.1: boron trifluoride diethyl etherate / dichloromethane / 39 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

11.2: 0.17 h / Cooling with ice

12.1: ethanol; potassium carbonate / acetonitrile / 12 h / 20 °C / Inert atmosphere

13.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -10 °C / Inert atmosphere

13.2: 4 h / -10 - 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; Hoveyda-Grubbs catalyst second generation; ethanol; trifluorormethanesulfonic acid; platinum oxide on carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; In tetrahydrofuran; methanol; hexanes; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;
DOI:10.1016/j.tet.2011.07.079

Reference yield:

: 1335101-42-2
tert-butyldimethyl((2S,3E,5E)-(1Ss)-(p-tolylsulfinyl)hepta-3,5-dien-2-yloxy)silane

: 1335101-38-6
(3R,4S)-4-((3S,4S,7S,8S)-4,7-bis(benzyloxy)-8-hydroxydeca-1,9-dien-3-yloxy)tetradec-1-en-3-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: water / toluene / 0.08 h / 20 °C

1.2: 2 h / 20 °C

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3.1: camphor-10-sulfonic acid / dichloromethane / 4 h / Inert atmosphere

4.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 96 h / Inert atmosphere; Reflux

5.1: platinum oxide on carbon; hydrogen / methanol; benzene / 24 h / 20 °C / 7500.75 Torr / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

7.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere

9.1: ethanol; magnesium; mercury dichloride / 4 h / 0 - 20 °C / Inert atmosphere

10.1: boron trifluoride diethyl etherate / dichloromethane / 39 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

10.2: 0.17 h / Cooling with ice

11.1: ethanol; potassium carbonate / acetonitrile / 12 h / 20 °C / Inert atmosphere

12.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -10 °C / Inert atmosphere

12.2: 4 h / -10 - 20 °C / Inert atmosphere

With n-butyllithium; Hoveyda-Grubbs catalyst second generation; ethanol; trifluorormethanesulfonic acid; platinum oxide on carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; In tetrahydrofuran; methanol; hexanes; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;
DOI:10.1016/j.tet.2011.07.079