(3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one
• CAS No.: 138332-40-8
• Molecular Formula: C₁₈H₂₇NO₃SSi
• Molecular Weight: 365.569
• Mol file: 138332-40-8.mol

Synonyms:(3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one

Chemical Property of (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one

There total 5 articles about (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)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: 59.0%

S-(trimethylsilyl)benzothioate (134987-61-4) + (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-phenylsulfinylazetidin-2-one (144069-72-7) → (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one (138332-40-8)

Guidance literature:

zinc(II) iodide; In acetonitrile; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)79927-8 DOI:10.1248/cpb.40.1733

Reference yield:

thiobenzoic acid (98-91-9) + (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone (85281-73-8) → (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one (138332-40-8)

Guidance literature:

In toluene; acetonitrile;

Reference yield:

thiobenzoic acid (98-91-9) + (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one (138332-40-8)

Guidance literature:

With sodium hydrogencarbonate; In acetone; at 60 ℃; for 4h;

DOI:10.1016/S0968-0896(97)00073-4

upstream raw materials:

(3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone

Copper(I) thiobenzoate

S-(trimethylsilyl)benzothioate

(3S,4R)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-phenylsulfinylazetidin-2-one

Downstream raw materials:

{(2R,3S)-2-Benzoylsulfanyl-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid allyl ester