Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl ester

Base Information

• Chemical Name: Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl ester
• CAS No.: 65794-41-4
• Molecular Formula: C₁₈H₂₂N₂O₇
• Molecular Weight: 378.382
• Mol file: 65794-41-4.mol

Synonyms:Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl ester

Chemical Property of Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl ester

There total 7 articles about Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl 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:

4-(2-hydroxyethyl)azetidin-2-one (64066-62-2) → (6RS)-2,2-dimethyl-7c-[(Ξ)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-(6rH)-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one (64066-68-8,65794-41-4,65794-46-9,71869-75-5,72690-82-5,72690-83-6,78339-96-5,86541-22-2,86833-65-0,86833-66-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (i) BF₃-Et₂O, CH₂Cl₂, (ii) /BRN= 505984/, LDA, THF

2: nBuLi / tetrahydrofuran

With n-butyllithium; In tetrahydrofuran;

DOI:10.1021/ja00469a069

Reference yield:

(6RS)-7c-((Ξ)-1-hydroxy-ethyl)-2,2-dimethyl-(6rH)-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one (64066-67-7,65794-44-7,65794-45-8,71869-74-4,72690-80-3,72690-81-4,77286-13-6,77286-14-7,77551-46-3,84276-74-4,84276-75-5,86541-19-7,86541-20-0,86541-21-1) + 4-nitrobenzyl chloroformate (4457-32-3) → (6RS)-2,2-dimethyl-7c-[(Ξ)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-(6rH)-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one (64066-68-8,65794-41-4,65794-46-9,71869-75-5,72690-82-5,72690-83-6,78339-96-5,86541-22-2,86833-65-0,86833-66-1)

Guidance literature:

With n-butyllithium; In tetrahydrofuran;

DOI:10.1021/ja00469a069

Reference yield:

4-(2-acetoxy-(E)-vinyl)-2-azetidinone (64221-82-5) → Carbonic acid (S)-1-((6R,7S)-2,2-dimethyl-8-oxo-3-oxa-1-aza-bicyclo[4.2.0]oct-7-yl)-ethyl ester 4-nitro-benzyl ester (65794-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd/C / ethyl acetate / 0.25 h / 25 °C / 2068.6 Torr

2: 96 percent / MeOH, MeONa / 2 h / 0 °C

3: 77 percent / BF₃*Et₂O / CH₂Cl₂ / 1.5 h / Ambient temperature

4: 89 percent / LDA / tetrahydrofuran / -78 °C

5: n-BuLi / tetrahydrofuran / 0.75 h / -78 °C / other carbinols

With methanol; n-butyllithium; boron trifluoride diethyl etherate; hydrogen; sodium methylate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo01294a042

upstream raw materials:

(6RS)-7c-((Ξ)-1-hydroxy-ethyl)-2,2-dimethyl-(6rH)-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one

4-nitrobenzyl chloroformate

4-(2-acetoxy-(E)-vinyl)-2-azetidinone

2,2-dimethyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one

Downstream raw materials:

Carbonic acid (R)-1-[(2S,3R)-2-(2-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester 4-nitro-benzyl ester