benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Base Information

Chemical Name:benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
CAS No.:15139-36-3
Molecular Formula:C₁₅H₁₇NO₄S
Molecular Weight:307.37
Hs Code.:
DSSTox Substance ID:DTXSID201105140
Nikkaji Number:J470.548C

Synonyms:SCHEMBL11096881;DTXSID201105140;15139-36-3

Suppliers and Price of benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Chemical Property:

XLogP3:2.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:307.08782920
Heavy Atom Count:21
Complexity:447

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1(C(N2C(S1)C(C2=O)O)C(=O)OCC3=CC=CC=C3)C
Isomeric SMILES:CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)O)C(=O)OCC3=CC=CC=C3)C

Technology Process of benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

There total 8 articles about benzyl (2S,5R,6R)-6-hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 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:

: 39126-59-5
6-oxopenicillanic acid benzyl ester

: 15139-36-3
6β-hydroxypenicillanic acid benzyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; ethanol;

Reference yield:

: 128971-90-4
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

: 15139-36-3,51056-25-8,128971-95-9
(2R,S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / 2,6-lutidine / tetrahydrofuran / 2 h / -78 °C

2: 1) ozone, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 15 min

3: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h

4: 62 percent / Et₃N, AcCl / CH₂Cl₂ / 20 h / 0 °C

5: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C

With 2,6-dimethylpyridine; dimethylsulfide; potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; triethylamine; acetyl chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00304a024

Reference yield:

: 128971-91-5
(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

: 15139-36-3,51056-25-8,128971-95-9
(2R,S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) ozone, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 2) 0 deg C, 15 min

2: 1) t-BuOK / 1) THF, t-BuOH, 0 deg C, 15 min, 2) 0 deg C, 40 h

3: 62 percent / Et₃N, AcCl / CH₂Cl₂ / 20 h / 0 °C

4: 1) tetrabutylammonium fluoride, 2) ozone / 1) THF, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C

With dimethylsulfide; potassium tert-butylate; tetrabutyl ammonium fluoride; ozone; triethylamine; acetyl chloride; In dichloromethane;
DOI:10.1021/jo00304a024