tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

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Chemical Name:tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate
CAS No.:1606140-72-0
Molecular Formula:C₂₈H₄₁NO₅
Molecular Weight:471.637
Hs Code.:

Synonyms:tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

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Chemical Property of tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

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Technology Process of tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

There total 4 articles about tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate 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:

: 1606140-68-4
tert-butyl (E)-5,5-diethoxypent-2-enoate

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: 1606140-72-0
tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

: tert-butyl (2S,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

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

tert-butyl (E)-5,5-diethoxypent-2-enoate; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With (1R)-(-)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h; Overall yield = 77 %; Overall yield = 4.57 g; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2014.03.055

Reference yield:

: 10601-80-6
ethyl 3,3-diethoxypropanoate

: 1606140-72-0
tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.83 h / -78 °C / Inert atmosphere

2.1: dichloromethane; toluene / 16 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

3.3: 12 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2014.03.055

Reference yield:

: 6367-37-9
3,3-diethoxypropanal

: 1606140-72-0
tert-butyl (2R,3R)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-5,5-diethoxypentanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dichloromethane; toluene / 16 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

2.3: 12 h / -78 - 20 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2014.03.055