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

Base Information

• Chemical Name: diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-hydroxy-1-buten-1-yl]-3-cephem-4-carboxylate
• CAS No.: 159492-74-7
• Molecular Formula: C₂₉H₃₂N₂O₆S
• Molecular Weight: 536.649

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

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

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

There total 1 articles about diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-hydroxy-1-buten-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: 70.0%

diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-tert-butyldimethylsilyloxy-1-buten-1-yl]-3-cephem-4-carboxylate (159492-73-6) → diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-hydroxy-1-buten-1-yl]-3-cephem-4-carboxylate (159492-74-7)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 1.5h;

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

Reference yield:

diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-hydroxy-1-buten-1-yl]-3-cephem-4-carboxylate (159492-74-7) → diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-carbamoyloxy-1-buten-1-yl]-3-cephem-4-carboxylate (159492-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 1 h / 5 °C

2: 2.9 g / silica gel / CHCl₃; methanol / 24 h / 20 °C

With silica gel; In methanol; dichloromethane; chloroform; 1: Addition / 2: Hydrolysis;

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

Reference yield:

diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-4-hydroxy-1-buten-1-yl]-3-cephem-4-carboxylate (159492-74-7) + Trichloroacetyl isocyanate (3019-71-4) → (6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(Z)-4-(2,2,2-trichloro-acetylcarbamoyloxy)-but-1-enyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:

In dichloromethane; at 5 ℃; for 1h;

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

upstream raw materials:

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

Downstream raw materials:

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

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