tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Base Information

Chemical Name:tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate
CAS No.:1393792-96-5
Molecular Formula:C₂₈H₃₉NO₄
Molecular Weight:453.622
Hs Code.:

Synonyms:tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

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Chemical Property of tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

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Technology Process of tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

There total 9 articles about tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 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: 39.0%

: 1393792-88-5
tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 1393792-97-6
tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

: 1393792-96-5
tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In diethyl ether; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate; In diethyl ether; hexane; at -20 ℃; for 5h; optical yield given as %de; Inert atmosphere;
DOI:10.1039/c2ob25099c

Reference yield:

: 1393792-88-5
tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate

: 17480-69-2
(S)-N-benzyl-1-phenylethylamine

: 1393792-94-3
tert-butyl (S,Z)-4,5-O-isopropylidene-4,5-dihydroxyhex-3-enoate

: 1393792-97-6
tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

: 1393792-96-5
tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In diethyl ether; hexane; at -20 ℃; for 0.5h; Inert atmosphere;

tert-butyl (4R,5S,E)-4,5-O-isopropylidene-4,5-dihydroxyhex-2-enoate; In diethyl ether; hexane; at -20 ℃; for 5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c2ob25099c

Reference yield:

: 4099-85-8,828937-29-7
((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

: 1393792-96-5
tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 1 h / 60 °C

2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

4.1: 1H-imidazole; iodine; triphenylphosphine / toluene; acetonitrile / 1 h / 60 °C

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Reflux; Inert atmosphere

6.1: 2.27% Pd/C; hydrogen; triethylamine / methanol / 24 h / 20 °C / 760.05 Torr

7.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -20 °C / Inert atmosphere

7.2: 5 h / -20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; Hoveyda-Grubbs catalyst second generation; 2.27% Pd/C; hydrogen; iodine; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; 1.1: Appel reaction / 4.1: Appel reaction;
DOI:10.1039/c2ob25099c