(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

Base Information

Chemical Name:(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid
CAS No.:288374-87-8
Molecular Formula:C₃₆H₆₀N₂O₉Si
Molecular Weight:692.966
Hs Code.:

(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

Synonyms:(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

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Chemical Property of (E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

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Technology Process of (E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

There total 14 articles about (E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid 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: 91.0%

: 288374-86-7
(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid allyl ester

: 288374-87-8
(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

Guidance literature:: With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

: 611-71-2
(R)-Mandelic Acid

: 288374-87-8
(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

Guidance literature:: Multi-step reaction with 13 steps

1.1: 100 percent / diethyl ether

2.1: Me₃Al / benzene; hexane / 0 - 20 °C

2.2: 93 percent / benzene / 20 °C

3.1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

4.1: 94 percent / tetrahydrofuran; diethyl ether / 5 h / 0 °C

5.1: diisopropylethylamine; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

5.2: 65 percent / CH₂Cl₂ / -78 - 0 °C

6.1: 87 percent / trichloroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

7.1: LiCl; diisopropylethylamine / acetonitrile / 0.08 h / 20 °C

7.2: 63 percent / acetonitrile / 4 h / 20 °C

8.1: 86 percent / KOH / tetrahydrofuran / 0 - 20 °C

9.1: cerium trichloride heptahydrate; sodium borohydride / ethanol / 2 h / 0 - 5 °C

10.1: 69 percent / tetramethylguanidinium azide / nitromethane / 5 h / 70 - 80 °C

11.1: Ph₃P / tetrahydrofuran; H₂O / 12 h / 50 - 60 °C

12.1: FDPP; diisopropylethylamine / dimethylformamide / 0.08 h / 20 °C

12.2: 149 mg / dimethylformamide / 4 h / 20 °C

13.1: 91 percent / tetrakistriphenylphosphine palladium; morpholine / tetrahydrofuran / 4 h / 20 °C

With morpholine; potassium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; di-n-butylboryl trifluoromethanesulfonate; pentafluorophenyl diphenyl-phosphinate; water; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetramethylguanidinum azide; lithium chloride; trichloroacetic acid; In tetrahydrofuran; diethyl ether; nitromethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Methylation / 2.1: Metallation / 2.2: Substitution / 3.1: silylation / 4.1: Grignard reaction / 5.1: Addition / 5.2: Condensation / 6.1: Hydrolysis / 7.1: deprotonation / 7.2: Condensation / 8.1: Tosylation / 9.1: Reduction / 10.1: Substitution / 11.1: Reduction / 12.1: deprotonation / 12.2: Acylation / 13.1: deallylation;
DOI:10.1016/S0040-4020(00)00255-6

Reference yield:

: 20698-91-3
(R)-methyl mandelate

: 288374-87-8
(E)-(5S,6S,7R,8R)-5-[(S)-2-((R)-3-tert-Butoxycarbonylamino-2-methyl-propionyloxy)-4-methyl-pentanoylamino]-8-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-6-methyl-8-phenyl-oct-2-enoic acid

Guidance literature:: Multi-step reaction with 12 steps

1.1: Me₃Al / benzene; hexane / 0 - 20 °C

1.2: 93 percent / benzene / 20 °C

2.1: 93 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

3.1: 94 percent / tetrahydrofuran; diethyl ether / 5 h / 0 °C

4.1: diisopropylethylamine; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

4.2: 65 percent / CH₂Cl₂ / -78 - 0 °C

5.1: 87 percent / trichloroacetic acid; water / CH₂Cl₂ / 1 h / 20 °C

6.1: LiCl; diisopropylethylamine / acetonitrile / 0.08 h / 20 °C

6.2: 63 percent / acetonitrile / 4 h / 20 °C

7.1: 86 percent / KOH / tetrahydrofuran / 0 - 20 °C

8.1: cerium trichloride heptahydrate; sodium borohydride / ethanol / 2 h / 0 - 5 °C

9.1: 69 percent / tetramethylguanidinium azide / nitromethane / 5 h / 70 - 80 °C

10.1: Ph₃P / tetrahydrofuran; H₂O / 12 h / 50 - 60 °C

11.1: FDPP; diisopropylethylamine / dimethylformamide / 0.08 h / 20 °C

11.2: 149 mg / dimethylformamide / 4 h / 20 °C

12.1: 91 percent / tetrakistriphenylphosphine palladium; morpholine / tetrahydrofuran / 4 h / 20 °C

With morpholine; potassium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; cerium(III) chloride; di-n-butylboryl trifluoromethanesulfonate; pentafluorophenyl diphenyl-phosphinate; water; trimethylaluminum; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetramethylguanidinum azide; lithium chloride; trichloroacetic acid; In tetrahydrofuran; diethyl ether; nitromethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 1.1: Metallation / 1.2: Substitution / 2.1: silylation / 3.1: Grignard reaction / 4.1: Addition / 4.2: Condensation / 5.1: Hydrolysis / 6.1: deprotonation / 6.2: Condensation / 7.1: Tosylation / 8.1: Reduction / 9.1: Substitution / 10.1: Reduction / 11.1: deprotonation / 11.2: Acylation / 12.1: deallylation;
DOI:10.1016/S0040-4020(00)00255-6