(3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-2-azetidinone
• CAS No.: 98729-69-2
• Molecular Formula: C₂₁H₂₁NO₃S
• Molecular Weight: 367.469
• Mol file: 98729-69-2.mol

Synonyms:(3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-2-azetidinone

Chemical Property of (3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-2-azetidinone

There total 7 articles about (3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-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: 88.0%

(3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-trimethylsilanylethynyl-azetidin-2-one (125829-49-4,131900-59-9) + diphenyldisulfane (882-33-7) → (3R,4R)-4-Ethynyl-3-((S)-1-hydroxy-ethyl)-1-(4-methoxy-benzyl)-azetidin-2-one (105620-49-3,105662-86-0,105662-87-1,105662-88-2,123537-16-6,123537-17-7) + (3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-phenylsulfanylethynyl-azetidin-2-one (98729-69-2,131900-60-2)

Guidance literature:

With copper(I) triflate; calcium carbonate; In tetrahydrofuran; 1,4-dioxane; for 1.8h; Heating;

DOI:10.1021/jo00294a002

Reference yield: 52.0%

(2S,3S)-2-((R)-1-Hydroxy-ethyl)-3-(4-methoxy-benzylamino)-5-trimethylsilanyl-pent-4-ynethioic acid S-phenyl ester (108053-20-9,121651-93-2,131900-51-1) → (3R,4R)-4-Ethynyl-3-((S)-1-hydroxy-ethyl)-1-(4-methoxy-benzyl)-azetidin-2-one (105620-49-3,105662-86-0,105662-87-1,105662-88-2,123537-16-6,123537-17-7) + (3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-phenylsulfanylethynyl-azetidin-2-one (98729-69-2,131900-60-2)

Guidance literature:

With copper(I) triflate; calcium carbonate; In 1,4-dioxane; benzene; for 0.666667h; Heating;

DOI:10.1021/jo00294a002

Reference yield: 51.0%

(2R,3R)-3-Methyl-oxirane-2-carboxylic acid (4-methoxy-benzyl)-(3-phenylsulfanyl-prop-2-ynyl)-amide (103841-76-5) → (3S,4S)-1-(p-methoxybenzyl)-3-<(R)-1-hydroxyethyl>-4-phenylthioethynyl-2-azetidinone (98729-69-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(00)88946-7

upstream raw materials:

(2S,3S)-2-((R)-1-Hydroxy-ethyl)-3-(4-methoxy-benzylamino)-5-trimethylsilanyl-pent-4-ynethioic acid S-phenyl ester

(2R,3R)-3-Methyl-oxirane-2-carboxylic acid (4-methoxy-benzyl)-(3-phenylsulfanyl-prop-2-ynyl)-amide

(3S,4S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-benzyl)-4-trimethylsilanylethynyl-azetidin-2-one

diphenyldisulfane