(2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 51056-25-8
• Molecular Formula: C₁₅H₁₇NO₄S
• Molecular Weight: 307.37
• Mol file: 51056-25-8.mol

Synonyms:(2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property of (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 16 articles about (2S,5R,6S)-Benzyl 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: 89.0%

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

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1021/jo00304a024

Reference yield:

6-Aminopenicillanic Acid (551-16-6) → (2S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (51056-25-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / 70percent HClO₄, NaNO₂ / H₂O / 0.33 h / -5 - 0 °C

2: 1) Et₃N / 1) DMF, 0 deg C, 2) rt, overnight

With perchloric acid; triethylamine; sodium nitrite; In water;

DOI:10.1021/jo00058a008

Reference yield:

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone (128971-90-4) → (2R,S,5R,6S)-Benzyl 6-Hydroxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (15139-36-3,51056-25-8,128971-95-9)

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

upstream raw materials:

6-α-hydroxypenicillanic acid

phenyldiazomethane

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

benzyl bromide

Downstream raw materials:

6α-methanesulfonyloxy-penicillanic acid benzyl ester

6α-acetoxy-penicillanic acid benzyl ester

6α-phenoxyacetoxy-penicillanic acid benzyl ester

6α-phenylacetoxy-penicillanic acid benzyl ester