(2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester
CAS No.:185146-31-0
Molecular Formula:C₃₀H₄₃NO₃S
Molecular Weight:497.742
Hs Code.:

Synonyms:(2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

There total 13 articles about (2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester 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:

: 64970-78-1
(2R,4R)-2-phenyl-1,3-thiazolidine-4-carboxylic acid

: 185146-31-0
(2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / Et₃N / methanol / 0.5 h / 50 °C

2: 80 percent / B₂H₆, Et₃N / tetrahydrofuran / 0.5 h / Ambient temperature

3: 72 percent / pyridine, CrO₃ / CH₂Cl₂ / 0.25 h

4: 1.) 1,1,1,3,3,3-hexamethylsilazane, n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 30 min, 2.) THF, HMPA, hexane, -78 deg C - 10 min, 0 deg C - 10 min

With pyridine; chromium(VI) oxide; n-butyllithium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; diborane; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja9629874

Reference yield:

: 18498-59-4
4-pentyn-1-al

: 185146-31-0
(2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

2: 1.) NaH / 1.) Et₂O, reflux, 1 h, 2.) Et₂O, reflux, 18 h

4: 1.) catecholborane, 2.) Pd(PPh₃)4, NaOH / 1.) 70-80 deg C, 2 h, 2.) THF, 70 deg C, 5 h

5: 1.) Et₃N, MsCl, 2.) NaI / 1.) CH₂Cl₂, -20 - (-10) deg C, 1 h, 2.) CH₂Cl₂, acetone, room temperature, 15 h

6: 87 percent / acetonitrile / 16 h / Heating

7: 1.) 1,1,1,3,3,3-hexamethylsilazane, n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 30 min, 2.) THF, HMPA, hexane, -78 deg C - 10 min, 0 deg C - 10 min

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; benzo[1,3,2]dioxaborole; In acetonitrile;
DOI:10.1021/ja9629874

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 185146-31-0
(2R,4R)-4-((1Z,5E,7E)-(R)-11-Methoxy-8-methyl-tetradeca-1,5,7,13-tetraenyl)-2-phenyl-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / (COCl)2, Et₃N / dimethylsulfoxide

3: 1.) NaH / 1.) Et₂O, reflux, 1 h, 2.) Et₂O, reflux, 18 h

5: 1.) catecholborane, 2.) Pd(PPh₃)4, NaOH / 1.) 70-80 deg C, 2 h, 2.) THF, 70 deg C, 5 h

6: 1.) Et₃N, MsCl, 2.) NaI / 1.) CH₂Cl₂, -20 - (-10) deg C, 1 h, 2.) CH₂Cl₂, acetone, room temperature, 15 h

7: 87 percent / acetonitrile / 16 h / Heating

8: 1.) 1,1,1,3,3,3-hexamethylsilazane, n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 30 min, 2.) THF, HMPA, hexane, -78 deg C - 10 min, 0 deg C - 10 min

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; sodium hydride; methanesulfonyl chloride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; sodium iodide; benzo[1,3,2]dioxaborole; In dimethyl sulfoxide; acetonitrile;
DOI:10.1021/ja9629874