(3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

Base Information

Chemical Name:(3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine
CAS No.:1268600-44-7
Molecular Formula:C₂₈H₄₃NO₄Si
Molecular Weight:485.739
Hs Code.:

Synonyms:(3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

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Chemical Property of (3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

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Technology Process of (3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

There total 4 articles about (3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine 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: 68.0%

: 1268600-41-4
(2R,3S)-2-(benzyloxy)methyl-1-bromo-3-(tert-butyldimethylsilyloxy)hex-5-en-1-yne

: 78888-18-3
N-tert-butoxycarbonylprop-2-en-1-amine

: 1268600-44-7
(3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

Guidance literature:: With potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; In toluene; at 80 - 85 ℃; for 46h; Inert atmosphere;
DOI:10.1021/jo2000308

Reference yield:

: (4S)-3-[(2R,3S)-3-hydroxy-2-[(benzyloxy)methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 1268600-44-7
(3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.83 h / 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.22 h / -78 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

3.2: 0.57 h / -78 - 0 °C / Inert atmosphere

4.1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 46 h / 80 - 85 °C / Inert atmosphere

With 2,6-dimethylpyridine; potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo2000308

Reference yield:

: 1268600-51-6
(4S)-3-[(2R,3S)-3-tert-butyldimethylsilyloxy-2-[(benzyloxy)-methyl]pent-4-en-oyl]-4-isopropyl-1,3-thiazolidine-2-thione

: 1268600-44-7
(3R,4S)-N-(tert-butoxycarbonyl)-N-(2-propenyl)hex-5-en-3-(benzyloxymethyl)-4-(tert-butyldimethylsilanyloxy)-1-ynylamine

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.22 h / -78 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

2.2: 0.57 h / -78 - 0 °C / Inert atmosphere

3.1: potassium phosphate; copper(ll) sulfate pentahydrate; 1,10-Phenanthroline / toluene / 46 h / 80 - 85 °C / Inert atmosphere

With potassium phosphate; 1,10-Phenanthroline; copper(ll) sulfate pentahydrate; potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jo2000308