(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

Base Information

Chemical Name:(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate
CAS No.:1089192-66-4
Molecular Formula:C₅₁H₅₇NO₆SSi
Molecular Weight:840.168
Hs Code.:

Synonyms:(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

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Chemical Property of (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

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Technology Process of (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

There total 12 articles about (S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate 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: 85.0%

: 1043577-31-6
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-amino-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

: 68858-20-8
Fmoc-Val-OH

: 1089192-66-4
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; Cooling with ice;
DOI:10.1021/jo801866z

Reference yield:

: 27144-18-9
3-(tritylthio) propanoic acid

: 1089192-66-4
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium tetrahydroborate / tetrahydrofuran / 0.17 h / 0 - 5 °C

1.2: 3 h / 0 - 30 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 2 h / -75 - -70 °C

2.2: 2 h / -75 - 5 °C

3.1: triphenylphosphine / toluene; water / 6 h / 25 - 105 °C

3.2: 2 h / 0 - 5 °C

4.1: diisobutylaluminium hydride / toluene / 3 h / 0 - 5 °C / Inert atmosphere

5.1: manganese(IV) oxide / dichloromethane / 8 h / 25 - 45 °C

6.1: titanium tetrachloride / dichloromethane / 0 - 5 °C

6.2: 2 h / -78 °C

6.3: 0.5 h / -78 °C

7.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 0 - 30 °C

8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0.92 h / 0 - 5 °C

9.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 6.16 h / 0 - 30 °C

With dmap; manganese(IV) oxide; sodium tetrahydroborate; oxalyl dichloride; lithium hydroxide monohydrate; water; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; toluene;

Reference yield:

: 180973-22-2
(2E)-5-[(triphenylmethyl)thio]-2-pentenal

: 1089192-66-4
(S,E)-2-(trimethylsilyl)ethyl 3-(((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl) amino)-3-methylbutanoyl)oxy)-7-(tritylthio)hept-4-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine; titanium tetrachloride / dichloromethane / -78 °C / Inert atmosphere

2: 1H-imidazole / dichloromethane / Inert atmosphere

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; titanium tetrachloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1016/j.bmc.2015.03.063