(2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester
• CAS No.: 69979-55-1
• Molecular Formula: C₁₇H₂₀BrNO₄S
• Molecular Weight: 414.32

Synonyms:(2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property of (2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

There total 3 articles about (2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 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:

6-diazopenicillanic acid benzyl ester (15058-70-5) → (5R)-6t-bromo-6c-((Ξ)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester (62263-85-8,62263-86-9,62263-87-0,69979-55-1,73788-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Br₂ / CH₂Cl₂

2: (i) MeMgBr, THF, Et₂O, (ii) /BRN= 505984/

With bromine; In dichloromethane;

DOI:10.1021/jo00438a003

Reference yield:

benzyl 6,6-dibromopenicillanate (35564-99-9) + acetaldehyde (75-07-0,9002-91-9) → (2S,5R,6S)-6-Bromo-6-(1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (69979-55-1)

Guidance literature:

With methyl magnesium iodide; Yield given. Multistep reaction; 1.) ether, -78 deg C, 20 min, 2.) 20 min;

Reference yield:

benzyl 6,6-dibromopenicillanate (35564-99-9) + acetaldehyde (75-07-0,9002-91-9) → (5R)-6t-bromo-6c-((Ξ)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]heptane-2c-carboxylic acid benzyl ester (62263-85-8,62263-86-9,62263-87-0,69979-55-1,73788-77-9)

Guidance literature:

Multistep reaction; (i) MeMgBr, THF, Et₂O, (ii) /BRN= 505984/;

DOI:10.1021/jo00438a003

upstream raw materials:

benzyl 6,6-dibromopenicillanate

acetaldehyde

6-diazopenicillanic acid benzyl ester

Downstream raw materials:

benzyl 6-alpha-(1-hydroxyethyl)penicillanate

2-{(2R,3R)-2-Acetoxy-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester

(2S,5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

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