2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester

Base Information

• Chemical Name: 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester
• CAS No.: 155899-89-1
• Molecular Formula: C₂₁H₃₀O₅S
• Molecular Weight: 394.532
• Mol file: 155899-89-1.mol

Synonyms:2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester

Chemical Property of 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester

There total 6 articles about 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic 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: 50.0%

2-[(1S,3S,5R)-3-((R)-Toluene-4-sulfinylmethyl)-2,8-dioxa-bicyclo[3.2.1]oct-1-yl]-propionic acid tert-butyl ester → 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester (155899-89-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1021/jo00093a022

Reference yield:

1-(tert-butyl) 6-ethyl 3-oxohexanedioate (93044-04-3) → 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester (155899-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / t-BuOK / 2-methyl-propan-2-ol / 1.) 25 deg C, 30 min, 2.) 20 min

2: 75 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

3: 60 percent / DIBAL / tetrahydrofuran; toluene / 0.25 h / -78 °C

4: 78 percent / (Me₄N)BH(OAc)3 / acetic acid / 0.5 h / Ambient temperature

5: 50 percent / 1 N HCl / tetrahydrofuran / 3 h / Ambient temperature

With hydrogenchloride; n-butyllithium; potassium tert-butylate; diisobutylaluminium hydride; diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; acetic acid; toluene; tert-butyl alcohol;

DOI:10.1021/jo00093a022

Reference yield:

(+)-(R)-1-(p-tolylsulfinyl)-2-propanone (66536-78-5) → 2-[(R)-5-[(S)-2-Hydroxy-3-((R)-toluene-4-sulfinyl)-propyl]-dihydro-furan-(2E)-ylidene]-propionic acid tert-butyl ester (155899-89-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / diisopropylamine, n-butyllithium / tetrahydrofuran; hexane / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

2: 60 percent / DIBAL / tetrahydrofuran; toluene / 0.25 h / -78 °C

3: 78 percent / (Me₄N)BH(OAc)3 / acetic acid / 0.5 h / Ambient temperature

4: 50 percent / 1 N HCl / tetrahydrofuran / 3 h / Ambient temperature

With hydrogenchloride; n-butyllithium; diisobutylaluminium hydride; diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; hexane; acetic acid; toluene;

DOI:10.1021/jo00093a022

upstream raw materials:

1-(tert-butyl) 6-ethyl 3-oxohexanedioate

(+)-(R)-1-(p-tolylsulfinyl)-2-propanone

tert-Butyl ethyl 3-oxo-2-methyladipate

tert-Butyl (+)-(R)-2-methyl-3,6,8-trioxo-9-(p-toluenesulfinyl)nonanoate