acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

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Chemical Name:acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester
CAS No.:234755-06-7
Molecular Formula:C₃₇H₄₄N₂O₆Si
Molecular Weight:640.852
Hs Code.:

Synonyms:acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

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Chemical Property of acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

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Technology Process of acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

There total 6 articles about acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester 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: 93.0%

: 108-24-7
acetic anhydride

: 234755-11-4
tert-butyl (1S,4R)-2-[N-(9H-fluoren-9-ylmethoxycarbonyl)-benzylamino]-(1-hydroxymethyl-4-trimethylsilylbut-3-ynyl)carbamate

: 234755-06-7
acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

Guidance literature:: With dmap; In chloroform; at 20 ℃;
DOI:10.3987/com-99-8481

Reference yield:

: 102308-32-7
(4S)-4-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 234755-06-7
acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 100 percent / 4 Angstroem mol. sieves / CH₂Cl₂ / 18 h / 4 °C

2.1: nBuLi / diethyl ether; hexane / 0.5 h / 0 °C

2.2: ZnCl₂ / diethyl ether; hexane / 0.5 h / 0 °C

2.3: 75 percent / diethyl ether; hexane / 18.5 h / -78 - 20 °C

3.1: 94 percent / (iPr₂)NEt / CH₂Cl₂ / 1 h / 0 °C

4.1: 53 percent / p-TsOH*H₂O / methanol / 16 h / 20 °C

5.1: 93 percent / DMAP / CHCl₃ / 20 °C

With dmap; n-butyllithium; 4 A molecular sieve; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; hexane; dichloromethane; chloroform; 1.1: Condensation / 2.1: Metallation / 2.2: Metallation / 2.3: Substitution / 3.1: Acylation / 4.1: Hydrolysis / 5.1: Acetylation;
DOI:10.3987/com-99-8481

Reference yield:

: 144492-44-4,144512-27-6
(4R)-benzyliminomethyl-2,2-dimethyloxazolidine-3-carboxylic acid 1,1-dimethylethyl ester

: 234755-06-7
acetic acid 3(S)-{benzyl[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2(R)-{[(tert-butoxy)carbonyl]amino}-5-(trimethylsilyl)pent-4-yn-1-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: nBuLi / diethyl ether; hexane / 0.5 h / 0 °C

1.2: ZnCl₂ / diethyl ether; hexane / 0.5 h / 0 °C

1.3: 75 percent / diethyl ether; hexane / 18.5 h / -78 - 20 °C

2.1: 94 percent / (iPr₂)NEt / CH₂Cl₂ / 1 h / 0 °C

3.1: 53 percent / p-TsOH*H₂O / methanol / 16 h / 20 °C

4.1: 93 percent / DMAP / CHCl₃ / 20 °C

With dmap; n-butyllithium; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; hexane; dichloromethane; chloroform; 1.1: Metallation / 1.2: Metallation / 1.3: Substitution / 2.1: Acylation / 3.1: Hydrolysis / 4.1: Acetylation;
DOI:10.3987/com-99-8481