(+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Base Information

• Chemical Name: (+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one
• CAS No.: 77447-99-5
• Molecular Formula: C₁₅H₁₆N₂O₇
• Molecular Weight: 336.301

Synonyms:(+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Chemical Property of (+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Chemical Property:

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Technology Process of (+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

There total 9 articles about (+/-)-4β-formylmethyl-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one 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: 79.0%

(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-98-4) → (+/-)-4β-formylmethyl-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-99-5)

Guidance literature:

With acetic acid; at 55 - 60 ℃; for 4h;

DOI:10.1039/P19810002282

Reference yield:

trans-4-methoxycarbonyl-3-(2',2'-dimethoxyethyl)-5-methylisoxazoline (72447-82-6,72843-52-8,78088-41-2,78778-11-7) → Carbonic acid 4-nitro-benzyl ester (S)-1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester (64066-71-3,67314-42-5,71869-79-9,72778-03-1,77447-99-5,80559-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 5.08 g / hydrogen / PtO₂ / acetic acid / 72 h / Ambient temperature

2: 10.1 percent / methylmagnesium iodide / diethyl ether; tetrahydrofuran / 18 h / Ambient temperature

3: 83 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4: AcOH, H₂O / 4.5 h / 60 °C

With dmap; methyl magnesium iodide; water; hydrogen; acetic acid; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid;

DOI:10.1021/ja00526a048

Reference yield:

(+/-)-4β-(2',2'-dimethoxyethyl)-3α-((1'R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (72789-82-3,72843-58-4,73890-31-0,73890-76-3,77447-98-4,78342-09-3,78822-11-4,79057-48-0,79299-23-3,79952-71-9) → Carbonic acid 4-nitro-benzyl ester (S)-1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester (64066-71-3,67314-42-5,71869-79-9,72778-03-1,77447-99-5,80559-32-6)

Guidance literature:

With water; acetic acid; at 60 ℃; for 4.5h;

DOI:10.1021/ja00526a048

upstream raw materials:

(+/-)-4β-(2',2'-dimethoxyethyl)-3α-((1'R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

methyl 3-amino-5-hydroxy-1,1-dimethoxyhexane-4-carboxylate

trans-4-<(2',2'-dimethoxy)ethyl>-3-<(1'R)-hydroxyethyl>azetidin-2-one

trans-4-methoxycarbonyl-3-(2',2'-dimethoxyethyl)-5-methylisoxazoline

Downstream raw materials:

(+/-)-3(R*)-(1(S*)-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethyl)-4(R*)-(3-(((p-nitrobenzyl)oxy)carbonyl)-2-chloro-3-(phenylthio)propyl)azetidin-2-one

(+/-)-3(R*)-(1(S*)-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethyl)-4(R*)-(3-(((p-nitrobenzyl)oxy)carbonyl)-3-chloro-2-(phenylthio)propyl)azetidin-2-one

(+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate

(+/-)-p-nitrobenzyl 6(R*)-(1(S*)-((((p-nitronbenzyl)oxy)carbonyl)oxy)ethyl)-2-(phenylthio)-1-carbapenam-3-carboxylate

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