(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone
• CAS No.: 78477-86-8
• Molecular Formula: C₁₄H₁₇NO₄
• Molecular Weight: 263.293
• Mol file: 78477-86-8.mol

Synonyms:(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

Chemical Property of (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone

There total 39 articles about (3S,4R)-3-<(R)-1-hydroxyethyl>-4-<(benzyloxycarbonyl)methyl>-2-azetidinone 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

<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

(2R,3S,4R)-4-Amino-2-methyl-6-oxo-tetrahydro-pyran-3-carboxylic acid

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

Downstream raw materials:

(3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

(5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

4-{(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-butyric acid 4-nitro-benzyl ester

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