[(1R)-1-[(2R,3S)-2-ethylsulfanylcarbothioylsulfanyl-4-oxoazetidin-3-yl]ethyl] 2,2,2-trichloroethyl carbonate

Base Information

• Chemical Name: [(1R)-1-[(2R,3S)-2-ethylsulfanylcarbothioylsulfanyl-4-oxoazetidin-3-yl]ethyl] 2,2,2-trichloroethyl carbonate
• CAS No.: 76431-30-6
• Molecular Formula: C11H14 Cl3 N O4 S3
• Molecular Weight: 426.793
• Nikkaji Number: J319.325J
• Mol file: 76431-30-6.mol

Synonyms:

Chemical Property of [(1R)-1-[(2R,3S)-2-ethylsulfanylcarbothioylsulfanyl-4-oxoazetidin-3-yl]ethyl] 2,2,2-trichloroethyl carbonate

Chemical Property:

• Boiling Point: 615.2±55.0 °C(Predicted)
• PKA: 12.05±0.60(Predicted)
• Density: 1.54±0.1 g/cm3(Predicted)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 424.915055
• Heavy Atom Count: 22
• Complexity: 447

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCSC(=S)SC1C(C(=O)N1)C(C)OC(=O)OCC(Cl)(Cl)Cl
• Isomeric SMILES: CCSC(=S)S[C@@H]1[C@H](C(=O)N1)[C@@H](C)OC(=O)OCC(Cl)(Cl)Cl

Technology Process of [(1R)-1-[(2R,3S)-2-ethylsulfanylcarbothioylsulfanyl-4-oxoazetidin-3-yl]ethyl] 2,2,2-trichloroethyl carbonate

There total 22 articles about [(1R)-1-[(2R,3S)-2-ethylsulfanylcarbothioylsulfanyl-4-oxoazetidin-3-yl]ethyl] 2,2,2-trichloroethyl carbonate 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: 85.0%

carbon disulfide (75-15-0,12122-00-8) + potassium ethanethiolate (54669-43-1) + methyl (2α,3β(R*))-2-chloro-α,4-dioxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate (76431-36-2) → Carbonic acid (R)-1-((2R,3S)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester (76431-30-6)

Guidance literature:

In ethanol;

DOI:10.1016/S0040-4039(01)81938-9

Reference yield:

1-(t-butyldimethylsilyl)-3-(1-hydroxyethyl)-4-ethylthioazetidin-2-one (76431-27-1) → Carbonic acid (S)-1-((2S,3R)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester (76431-30-6,76496-42-9,76496-43-0,80629-52-3,80629-60-3,80629-61-4,80629-65-8,80629-66-9,89395-50-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: acidic desilylation

3: Cl₂ / -20 °C

4: aq. ethanol / 0 °C

With pyridine; chlorine; In ethanol;

DOI:10.1016/S0040-4039(01)81939-0

Reference yield:

Carbonic acid 1-(2-ethylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester (76431-29-3) → Carbonic acid (S)-1-((2S,3R)-2-ethylsulfanylthiocarbonylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester (76431-30-6,76496-42-9,76496-43-0,80629-52-3,80629-60-3,80629-61-4,80629-65-8,80629-66-9,89395-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Cl₂ / -20 °C

2: aq. ethanol / 0 °C

With chlorine; In ethanol;

DOI:10.1016/S0040-4039(01)81939-0

upstream raw materials:

methyl (3S,5R,6R)-6-<(R)-1-hydroxyethyl>penicillanate

carbon disulfide

potassium ethanethiolate

methyl (2α,3β(R*))-2-chloro-α,4-dioxo-3-(1-{[(2,2,2-trichloroethoxy)carbonyl]oxy}ethyl)azetidine-1-acetate

Downstream raw materials:

{(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

{(2R,3S)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(S)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

(5R,6S)-3-Ethylsulfanyl-6-((S)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

{(2R,3R)-2-Ethylsulfanylthiocarbonylsulfanyl-4-oxo-3-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

Refernces

• 1、 McCombie, S. W.,Ganguly, A. K.,Girijavallabhan, V. M.,Jeffrey, P. D.,Lin, S.,at al.. "SYNTHESIS OF RACEMIC, 2-(ALKYLTHIO)-6-(1-HYDROXYETHYL) PENEMS; ATTEMPTED PENEM SYNTHESIS VIA COPPER (I) - PROMOTED CYCLISATIONS". . p. 3489 - 3492. Retrieved 2007/10/02.