(R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester

Base Information

• Chemical Name: (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester
• CAS No.: 83541-79-1
• Molecular Formula: C₁₈H₂₃ClN₂O₃S
• Molecular Weight: 382.911
• Mol file: 83541-79-1.mol

Synonyms:(R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester

Chemical Property of (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester

There total 15 articles about (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl 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: 68.0%

methanol (67-56-1) + (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic acid (83486-95-7) → (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester (83541-79-1)

Guidance literature:

With thionyl chloride;

DOI:10.1002/bscb.19820911203

Reference yield:

hex-5-in-carboxyl chloride (55183-45-4) → (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester (83541-79-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / pyridine; CH₂Cl₂ / 0 °C

2: 65 percent / Zn / acetic acid

3: 95 percent / diisobutylaluminum hydride / toluene / -78 °C

4: 72 percent / CH₂Cl₂

5: 63 percent / BaO / toluene / Heating; further reagent

6: Zn, AcOH / H₂O / 70 °C

7: Na₂CO₃ / tetrahydrofuran / 0 °C

8: 87 percent / Ba(OH)2 / dioxane; H₂O / Heating

9: SOCl₂ / diethyl ether

With barium dihydroxide; thionyl chloride; diisobutylaluminium hydride; sodium carbonate; acetic acid; barium(II) oxide; zinc; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; dichloromethane; water; acetic acid; toluene;

DOI:10.1021/ja00387a057

Reference yield:

(1S,4R,10R,13R)-2-Benzyl-3-oxa-12-thia-2,9-diaza-tricyclo[8.3.0.04,13]tridecan-8-one (78841-16-4,83541-77-9) → (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-chloro-pentanoic acid methyl ester (83541-79-1)

Guidance literature:

Multi-step reaction with 5 steps

1: Zn, AcOH / H₂O / 70 °C

2: Na₂CO₃ / tetrahydrofuran / 0 °C

3: 87 percent / Ba(OH)2 / dioxane; H₂O / Heating

4: SOCl₂ / diethyl ether

With barium dihydroxide; thionyl chloride; sodium carbonate; acetic acid; zinc; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water;

DOI:10.1021/ja00387a057

upstream raw materials:

methanol

(R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic acid

hex-5-in-carboxyl chloride

N-benzylhydroxylamine hydrochloride

Downstream raw materials:

<3aS-(3aα,4β,6aα)>-Hexahydro-2-oxo-3-(phenylmethyl)-1H-thieno<3,4-d>imidazole-4-pentanoic acid methyl ester

biotin