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

Base Information

Chemical Name:tert-butyl (1S,4R)-2-[N-(9H-fluoren-9-ylmethoxycarbonyl)-benzylamino]-(1-hydroxymethyl-4-trimethylsilylbut-3-ynyl)carbamate
CAS No.:234755-11-4
Molecular Formula:C₃₅H₄₂N₂O₅Si
Molecular Weight:598.814
Hs Code.:

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

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

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

There total 5 articles about tert-butyl (1S,4R)-2-[N-(9H-fluoren-9-ylmethoxycarbonyl)-benzylamino]-(1-hydroxymethyl-4-trimethylsilylbut-3-ynyl)carbamate 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: 53.0%

: 234755-10-3
tert-butyl (1S,4R)-[1-benzyl-(9H-fluoren-9-ylmethoxycarbonylamino)]-2,2-dimethyloxazolidine-3-carboxylate

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

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 16h;
DOI:10.3987/com-99-8481

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With n-butyllithium; 4 A molecular sieve; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; hexane; dichloromethane; 1.1: Condensation / 2.1: Metallation / 2.2: Metallation / 2.3: Substitution / 3.1: Acylation / 4.1: Hydrolysis;
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

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

Guidance literature:: Multi-step reaction with 3 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

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