diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate

Base Information

• Chemical Name: diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate
• CAS No.: 130516-13-1
• Molecular Formula: C₃₁H₂₈N₂O₅S
• Molecular Weight: 540.64

Synonyms:diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate

Chemical Property of diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate

Chemical Property:

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Technology Process of diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate

There total 13 articles about diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-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: 75.0%

Diphenylmethyl 2-<(3R,4R)-4-<(p-toluenesulfonyl)thio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate (143159-86-8) → diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate (130516-13-1) + diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-2-em-4-carboxylate

Guidance literature:

In tetrahydrofuran; at -100 ℃; for 0.25h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92503-6

Reference yield: 55.0%

Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate (143159-88-0) → diphenylmethyl (6R,7R)-3-methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate (10209-10-6) + diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate (130516-13-1) + (6R,7R)-3-(Benzothiazol-2-ylsulfanyl)-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92503-6

Reference yield: 29.0%

Lithium-di-cis-1-propenylcuprat + diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>ceph-3-em-4-carboxylate (130516-07-3) → diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate (130516-13-1)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)97404-5

upstream raw materials:

(Z)-1-propenyl bromide

Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate

(Z)-1-propenyllithium

diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>ceph-3-em-4-carboxylate

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