methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate

Base Information

• Chemical Name: methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate
• CAS No.: 307990-71-2
• Molecular Formula: C₁₇H₂₀N₂O₆
• Molecular Weight: 348.356

Synonyms:methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate

Chemical Property of methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate

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Technology Process of methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate

There total 2 articles about methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate 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: 54.0%

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde (89969-26-6) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate (307990-71-2)

Guidance literature:

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde; methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride; With pyridine; at 20 ℃; for 240h;

With potassium carbonate; In methanol; Further stages.;

DOI:10.1021/jo000416v

Reference yield: 19.0%

(S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde (89969-26-6) + methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride (5680-80-8) → methyl (3R,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate + methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate (307990-71-2) + methyl (3S,6R,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate

Guidance literature:

With triethylamine; In toluene; for 48h; Heating;

DOI:10.1021/jo000416v

Reference yield: 95.0%

methyl (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylate (307990-71-2) → (3S,6S,9S)-3-benzyloxycarbonylamino-2-oxo-7,1-oxazabicyclo[4.3.0]nonane-9-carboxylic acid

Guidance literature:

With sodium hydroxide; In ethanol; at 0 ℃; for 1h;

DOI:10.1021/jo000416v

upstream raw materials:

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

methyl (2S)-2-amino-3-hydroxypropanoate hydrochloride

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