diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

Base Information

Chemical Name:diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate
CAS No.:158743-85-2
Molecular Formula:C₃₄H₃₂N₆O₆S₄
Molecular Weight:748.929
Hs Code.:

Synonyms:diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

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Chemical Property of diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

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Technology Process of diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

There total 6 articles about diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-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: 34.3%

: 36923-21-4
diphenylmethyl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

: 2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoic acid

: 158743-85-2
diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

: diphenylmethyl 7β-<(E)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

Guidance literature:: With 4-methyl-morpholine; P,P-dichlorophenylphosphine oxide; In dichloromethane; at -30 - -20 ℃; for 2h;
DOI:10.7164/antibiotics.47.453

Reference yield:

: diphenylmethyl 2-(2-tert-butoxycarbonylaminothiazol-4-yl)acetate

: 158743-85-2
diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) 1M lithium hexamethyldisilazane / 1.) THF, -78 deg C, 30 min, 2.) THF, 1 h

2: 65 percent / ethanol / 2 h / 0 °C

3: NaBH₄ / methanol; CH₂Cl₂ / 0.33 h / -20 °C

4: 1.) TEA, methanesulfonyl chloride, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, ice-water cooling, 30 min, 2.) CH₂Cl₂, ice-water cooling, 20 min

5: 78 percent / trifluoroacetic acid / CH₂Cl₂; various solvent(s) / 2 h / 0 - 5 °C

6: 11 percent / N-methylmorpholine, phenylphosphoryl dichloride / CH₂Cl₂ / 2 h / -30 - -20 °C

With 4-methyl-morpholine; P,P-dichlorophenylphosphine oxide; sodium tetrahydroborate; TEA; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium hexamethyldisilazane; In methanol; ethanol; dichloromethane;
DOI:10.7164/antibiotics.47.453

Reference yield:

: 158743-65-8
2-(2-tert-Butoxycarbonylamino-thiazol-4-yl)-4-chloro-3-oxo-butyric acid benzhydryl ester

: 158743-85-2
diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 65 percent / ethanol / 2 h / 0 °C

2: NaBH₄ / methanol; CH₂Cl₂ / 0.33 h / -20 °C

3: 1.) TEA, methanesulfonyl chloride, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) CH₂Cl₂, ice-water cooling, 30 min, 2.) CH₂Cl₂, ice-water cooling, 20 min

4: 78 percent / trifluoroacetic acid / CH₂Cl₂; various solvent(s) / 2 h / 0 - 5 °C

5: 11 percent / N-methylmorpholine, phenylphosphoryl dichloride / CH₂Cl₂ / 2 h / -30 - -20 °C

With 4-methyl-morpholine; P,P-dichlorophenylphosphine oxide; sodium tetrahydroborate; TEA; methanesulfonyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; ethanol; dichloromethane;
DOI:10.7164/antibiotics.47.453