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

Base Information

• Chemical Name: (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic acid
• CAS No.: 83486-95-7
• Molecular Formula: C₁₇H₂₂N₂O₄S
• Molecular Weight: 350.439
• Mol file: 83486-95-7.mol

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

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

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-hydroxy-pentanoic acid

There total 12 articles about (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic 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: 87.0%

Benzyl-((1R,7R,8R,11S)-7-hydroxy-3-oxo-9-thia-2-aza-bicyclo[6.2.1]undec-11-yl)-carbamic acid methyl ester (83541-78-0) → (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic acid (83486-95-7)

Guidance literature:

With barium dihydroxide; In 1,4-dioxane; water; Heating;

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-hydroxy-pentanoic acid (83486-95-7)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1021/ja00387a057

Reference yield:

N-benzylhydroxylamine hydrochloride (29601-98-7) → (R)-5-((3aR,6R,6aS)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-5-hydroxy-pentanoic acid (83486-95-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / CH₂Cl₂

2: 63 percent / BaO / toluene / Heating; further reagent

3: Zn, AcOH / H₂O / 70 °C

4: Na₂CO₃ / tetrahydrofuran / 0 °C

5: 87 percent / Ba(OH)2 / dioxane; H₂O / Heating

With barium dihydroxide; sodium carbonate; acetic acid; barium(II) oxide; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1021/ja00387a057

upstream raw materials:

Benzyl-((1R,7R,8R,11S)-7-hydroxy-3-oxo-9-thia-2-aza-bicyclo[6.2.1]undec-11-yl)-carbamic acid methyl ester

hex-5-in-carboxyl chloride

N-benzylhydroxylamine hydrochloride

(1R,7R,8R,11S)-11-Benzylamino-7-hydroxy-9-thia-2-aza-bicyclo[6.2.1]undecan-3-one

Downstream raw materials:

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

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

biotin