(2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 229490-05-5
• Molecular Formula: C₂₄H₂₂N₂O₆S
• Molecular Weight: 466.514

Synonyms:(2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property of (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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Technology Process of (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 7 articles about (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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: 65.0%

(2S,3S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229490-02-2) → (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229490-05-5)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; ammonium fluoride; hydrogen fluoride; In N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00107-9

Reference yield:

diphenylmethyl 6β-(hydroxymethyl)penicillanate (76517-80-1) → (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229490-05-5)

Guidance literature:

Multi-step reaction with 9 steps

2: AcOH, H₂O₂

3: 100 percent / toluene

4: AcOAg / CH₂Cl₂

5: KMnO₄, AcOH

6: 97 percent / thiourea, pyridine / dimethylformamide

7: 64 percent / pyridinium chlorochromate

8: 46 percent

9: 65 percent / NH₄F*HF, NMP / dimethylformamide

With pyridine; 1-methyl-pyrrolidin-2-one; ammonium fluoride; potassium permanganate; hydrogen fluoride; dihydrogen peroxide; silver(I) acetate; acetic acid; thiourea; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(99)00107-9

Reference yield:

diphenylmethyl 6β-(t-butyldimethylsilyloxymethyl)penicillanate (81324-30-3) → (2S,3S,5R,6R)-3-((Z)-2-Cyano-vinyl)-6-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (229490-05-5)

Guidance literature:

Multi-step reaction with 8 steps

1: AcOH, H₂O₂

2: 100 percent / toluene

3: AcOAg / CH₂Cl₂

4: KMnO₄, AcOH

5: 97 percent / thiourea, pyridine / dimethylformamide

6: 64 percent / pyridinium chlorochromate

7: 46 percent

8: 65 percent / NH₄F*HF, NMP / dimethylformamide

With pyridine; 1-methyl-pyrrolidin-2-one; ammonium fluoride; potassium permanganate; hydrogen fluoride; dihydrogen peroxide; silver(I) acetate; acetic acid; thiourea; pyridinium chlorochromate; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(99)00107-9

upstream raw materials:

(2S,3S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((Z)-2-cyano-vinyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

diphenylmethyl 6β-(hydroxymethyl)penicillanate

diphenylmethyl 6β-(t-butyldimethylsilyloxymethyl)penicillanate

(2S,3R,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-3-formyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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