diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate

Base Information

• Chemical Name: diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate
• CAS No.: 163347-95-3
• Molecular Formula: C₃₄H₃₄N₂O₆S
• Molecular Weight: 598.72

Synonyms:diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate

Chemical Property of diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate

Chemical Property:

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Technology Process of diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate

There total 2 articles about diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-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:

diphenylmethyl 7β-tert-butoxycarbonylamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate iodide → diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate (163347-95-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH; NaCl / CH₂Cl₂; H₂O / 0.75 h / 20 °C

2: 7.2 g / CH₂Cl₂ / 20 °C

With sodium hydroxide; sodium chloride; In dichloromethane; water; 1: Dehydroiodination / 2: Wittig reaction;

DOI:10.1016/S0968-0896(99)00257-6

Reference yield:

(6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ5-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (143159-43-7) + 2-phenoxyethanal (2120-70-9) → diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate (163347-95-3)

Guidance literature:

In dichloromethane; at 20 ℃;

DOI:10.1016/S0968-0896(99)00257-6

Reference yield: 81.0%

trifluoroacetic acid (76-05-1) + diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylate (163347-95-3) → 7β-amino-3-[(Z)-3-phenoxy-1-propen-1-yl]-3-cephem-4-carboxylic acid trifluoroacetate

Guidance literature:

With methoxybenzene; In dichloromethane; at 20 ℃;

DOI:10.1016/S0968-0896(99)00257-6

upstream raw materials:

(6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

2-phenoxyethanal

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