[(2R,3S)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester

Base Information

• Chemical Name: [(2R,3S)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester
• CAS No.: 84985-44-4
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293

Synonyms:[(2R,3S)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester

Chemical Property of [(2R,3S)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester

Chemical Property:

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Technology Process of [(2R,3S)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester

There total 8 articles about [(2R,3S)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid 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: 97.0%

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-acetic acid benzyl ester → (3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester (77120-96-8,78477-86-8,78919-18-3,84985-44-4,89615-92-9)

Guidance literature:

With titanium tetrachloride; ethyl acetate; In dichloromethane; at 0 - 5 ℃; for 4h;

DOI:10.1021/jo0604484

Reference yield: 92.0%

(2S,3R)-3-Amino-2-((S)-1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride (77120-95-7,78419-61-1,78919-17-2,112020-76-5) → benzyl -4-oxoazetidin-2-yl> acetate (77120-96-8,78477-86-8,78919-18-3,84985-44-4,89615-92-9)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In acetonitrile; at 60 ℃; for 4h;

DOI:10.1016/S0040-4039(00)78606-0

Reference yield: 88.0%

3-Amino-2-(1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride (77120-95-7,78419-61-1,78919-17-2,112020-76-5) → (3SR,4RS)-3-[1(SR)-hydroxyethyl]-2-oxoazetidine-4-yl-acetic acid benzyl ester (77120-96-8,78477-86-8,78919-18-3,84985-44-4,89615-92-9)

Guidance literature:

With triethylamine; dicyclohexyl-carbodiimide; In benzyl alcohol; at 55 ℃; for 4.5h;

DOI:10.1016/0040-4039(81)89007-7

upstream raw materials:

3-Amino-2-(1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride

(2S,3R)-3-Amino-2-((S)-1-hydroxy-ethyl)-pentanedioic acid 5-benzyl ester; hydrochloride

benzyl chloride

(E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester

Downstream raw materials:

{(2R,3S)-4-Oxo-3-[1-(piperidine-1-sulfinyloxy)-ethyl]-azetidin-2-yl}-acetic acid benzyl ester

[(2R,3S)-3-(1-Diethylsulfinamoyloxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester

(E)-3-(3-Butyl-ureido)-hex-4-enoic acid benzyl ester

[(2R,3R)-3-((R)-1-Fluoro-ethyl)-4-oxo-azetidin-2-yl]-acetic acid benzyl ester

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