(3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

Base Information

• Chemical Name: (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS No.: 160248-47-5
• Molecular Formula: C₁₆H₁₈N₂O₅S
• Molecular Weight: 350.395
• Mol file: 160248-47-5.mol

Synonyms:(3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

Chemical Property of (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid

There total 5 articles about (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic 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:

(2R,5S,8S)-1-aza-8-benzyloxycarbonylamino-9-oxo-4-thiabicyclo[3.4.0]nonane-2-carboxylic acid methyl ester (131990-88-0) → (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid (160248-47-5)

Guidance literature:

With sodium hydroxide; In methanol; at 0 ℃; for 4h;

DOI:10.1021/ja00102a008

Reference yield:

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester (58456-26-1) → (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid (160248-47-5)

Guidance literature:

Multi-step reaction with 4 steps

1: Bu₃SnH / ethyl acetate / 14 h / 0 - 20 °C

2: 71 percent / pyridine / 120 h / Ambient temperature

3: 66 percent / Na₂CO₃ / methanol / 4 h / Ambient temperature

4: 1 N aq. NaOH / methanol / 4 h / 0 °C

With pyridine; sodium hydroxide; tri-n-butyl-tin hydride; sodium carbonate; In methanol; ethyl acetate;

DOI:10.1021/ja00102a008

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → (3R,6S,8aS)-6-Benzyloxycarbonylamino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid (160248-47-5)

Guidance literature:

Multi-step reaction with 5 steps

1: (COCl)2, DMF / CH₂Cl₂ / 14 h / Ambient temperature

2: Bu₃SnH / ethyl acetate / 14 h / 0 - 20 °C

3: 71 percent / pyridine / 120 h / Ambient temperature

4: 66 percent / Na₂CO₃ / methanol / 4 h / Ambient temperature

5: 1 N aq. NaOH / methanol / 4 h / 0 °C

With pyridine; sodium hydroxide; oxalyl dichloride; tri-n-butyl-tin hydride; sodium carbonate; N,N-dimethyl-formamide; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja00102a008

upstream raw materials:

(2R,5S,8S)-1-aza-8-benzyloxycarbonylamino-9-oxo-4-thiabicyclo[3.4.0]nonane-2-carboxylic acid methyl ester

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde

(S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

Downstream raw materials:

Fmoc-β-turn-dipeptide