(E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

Base Information

Chemical Name:(E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene
CAS No.:194149-71-8
Molecular Formula:C₃₁H₅₃NO₄Si
Molecular Weight:531.852
Hs Code.:

Synonyms:(E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

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Chemical Property of (E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

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Technology Process of (E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

There total 12 articles about (E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene 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: 84.0%

: 180133-61-3
(4R,5S)-4-methyl-5-methoxy-6-phenyl-2-hexyne

: 194149-66-1
(E)-(3R,4S)-1-iodo-3-(N-tert-butoxycarbonyl)amino-5-(tert-butyldimethylsiloxy)-4-methyl-pent-1-ene

: 194149-71-8
(E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

Guidance literature:: (4R,5S)-4-methyl-5-methoxy-6-phenyl-2-hexyne; With Schwartz's reagent; In tetrahydrofuran; at 20 - 50 ℃; for 0.916667h;

With zinc(II) chloride; In tetrahydrofuran; at 20 ℃; for 0.0333333h;

(E)-(3R,4S)-1-iodo-3-(N-tert-butoxycarbonyl)amino-5-(tert-butyldimethylsiloxy)-4-methyl-pent-1-ene; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 20 ℃; for 0.0833333h; Further stages.;
DOI:10.1021/ja0206700

Reference yield: 84.0%

: 194149-66-1
(E)-(3R,4S)-1-iodo-3-(N-tert-butoxycarbonyl)amino-5-(tert-butyldimethylsiloxy)-4-methyl-pent-1-ene

: C₆H₅CH₂CH(OCH₃)CH(CH₃)CHC(CH₃)ZnCl

: 194149-71-8
(E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 0.0833333h; Ambient temperature;
DOI:10.1021/jo9706483

Reference yield:

: (E)-(4S,5S)-4-Amino-6-(tert-butyl-dimethyl-silanyloxy)-5-methyl-hex-2-enoic acid methyl ester

: 194149-71-8
(E,E)-(2S,3S,8S,9S)-3-(N-tert-butoxycarbonyl)amino-1-(tert-butyl-dimethylsiloxy)-9-methoxy-10-phenyl-2,6,8-trimethyl-4,6-decadiene

Guidance literature:: Multi-step reaction with 4 steps

1.1: aq. NaHCO₃ / dioxane / 14 h / 20 °C

2.1: O₃; pyridine / methanol / -78 °C

2.2: Me₂S / 4 h / 20 °C

3.1: 973 mg / CrCl₂ / tetrahydrofuran / 5 h / 20 °C

4.1: Cp₂Zr(H)Cl / tetrahydrofuran / 0.92 h / 20 - 50 °C

4.2: ZnCl₂ / tetrahydrofuran / 0.03 h / 20 °C

4.3: 84 percent / Pd(PPh₃)4 / 0.08 h / 20 °C

With pyridine; chromium dichloride; Schwartz's reagent; sodium hydrogencarbonate; ozone; In tetrahydrofuran; 1,4-dioxane; methanol;
DOI:10.1021/ja0206700