(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

Base Information

Chemical Name:(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid
CAS No.:173251-21-3
Molecular Formula:C₂₇H₃₉NO₄S
Molecular Weight:473.677
Hs Code.:

Synonyms:(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

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Chemical Property of (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

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Technology Process of (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

There total 7 articles about (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid 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:

: 173251-18-8
(2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenal

: 173251-21-3
(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

Guidance literature:: Multi-step reaction with 4 steps

1: CrCl₂, Ni(COD)2 / tetrahydrofuran / Ambient temperature

2: 77 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

3: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) THF, -20 deg C to room temperature, 2.) THF, -78 deg C, 20 min

4: aq. LiOH / dioxane / 23 h / Ambient temperature

With chromium dichloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium hydroxide; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo981892c

Reference yield:

: 173251-17-7
(2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenol

: 173251-21-3
(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) (COCl)2, DMSO, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) -60 deg C to room temperature

2: CrCl₂, Ni(COD)2 / tetrahydrofuran / Ambient temperature

3: 77 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

4: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) THF, -20 deg C to room temperature, 2.) THF, -78 deg C, 20 min

5: aq. LiOH / dioxane / 23 h / Ambient temperature

With chromium dichloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium hydroxide; oxalyl dichloride; TEA; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane;
DOI:10.1021/jo981892c

Reference yield:

: methyl (2R/S,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenoate

: 173251-21-3
(2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 68 percent / DIBAL / toluene; hexane / 0.25 h / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) TEA / 1.) CH₂Cl₂, -60 deg C, 10 min, 2.) -60 deg C to room temperature

3: CrCl₂, Ni(COD)2 / tetrahydrofuran / Ambient temperature

4: 77 percent / Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

5: 1.) CuCN, 2.) BF₃*OEt₂ / 1.) THF, -20 deg C to room temperature, 2.) THF, -78 deg C, 20 min

6: aq. LiOH / dioxane / 23 h / Ambient temperature

With chromium dichloride; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium hydroxide; oxalyl dichloride; TEA; boron trifluoride diethyl etherate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; toluene;
DOI:10.1021/jo981892c