(6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Base Information

• Chemical Name: (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester
• CAS No.: 35409-23-5
• Molecular Formula: C₂₄H₂₇N₅O₉S
• Molecular Weight: 561.572

Synonyms:

Chemical Property of (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

There total 1 articles about (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl 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:

Chloromethyl pivalate (18997-19-8) + (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid; potassium salt → (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (35409-23-5)

Guidance literature:

Multistep reaction; (i), (ii) MCPBA;

DOI:10.7164/antibiotics.24.767

Reference yield:

(6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (35409-23-5) → (6R)-3-acetoxymethyl-7t-((R)-2-amino-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: Na₂S₂O₄, AcCl

2: H₂ / Pd-C

With sodium dithionite; hydrogen; acetyl chloride; palladium on activated charcoal;

DOI:10.7164/antibiotics.24.767

Reference yield:

(6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-5ξ,8-dioxo-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (35409-23-5) → (6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester (24644-09-5)

Guidance literature:

With sodium dithionite; acetyl chloride;

DOI:10.7164/antibiotics.24.767

upstream raw materials:

Chloromethyl pivalate

Downstream raw materials:

(6R)-3-acetoxymethyl-7t-((R)-2-azido-2-phenyl-acetylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester

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