tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

Base Information

Chemical Name:tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate
CAS No.:1605346-71-1
Molecular Formula:C₃₅H₄₅NO₅
Molecular Weight:559.746
Hs Code.:

Synonyms:tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

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Chemical Property of tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

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Technology Process of tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

There total 12 articles about tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate 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:

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

: 1605346-52-8
tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

: 1605346-65-3
tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

: 1605346-71-1
tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

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-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate; In diethyl ether; hexane; at -20 ℃; for 5h; Overall yield = 79 %; Overall yield = 820 mg; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2014.02.004

Reference yield:

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

: 1605346-52-8
tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate

: 1605346-65-3
tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

: 1605346-56-2
C₂₀H₂₈O₅

: 1605346-71-1
tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

Guidance literature:: (S)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

tert-butyl (4R,5S,E)-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhex-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2014.02.004

Reference yield:

: 155934-55-7
(4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

: 1605346-65-3
tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

: 1605346-71-1
tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-dihydroxy-4,5-O-isopropylidene-6-benzyloxyhexanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / hexane; tetrahydrofuran / 16 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / Petroleum ether; tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

2.2: 16 h / 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Reflux; Inert atmosphere

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

4.2: 5 h / -20 °C / Inert atmosphere

With n-butyllithium; Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; Petroleum ether;
DOI:10.1016/j.tetasy.2014.02.004