tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

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Chemical Name:tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate
CAS No.:1606140-67-3
Molecular Formula:C₂₇H₃₉NO₅
Molecular Weight:457.61
Hs Code.:

Synonyms:tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

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Chemical Property of tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

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Technology Process of tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

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

: 1613225-08-3
C₂₇H₃₇NO₅

: 1606140-67-3
tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

: 1606140-44-6
tert-butyl (2R,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

Guidance literature:: With sodium tetrahydroborate; In methanol; at -20 - 20 ℃; Reagent/catalyst; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2014.03.055

Reference yield:

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 1606140-67-3
tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 22 h / Reflux; Inert atmosphere

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

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 - 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / -20 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; methanol; hexane; dichloromethane; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1016/j.tet.2014.03.055

Reference yield:

: 1606140-38-8
tert-butyl (E)-4,4-diethoxybut-2-enoate

: 1606140-67-3
tert-butyl (2S,3S)-2-hydroxy-3-{N-benzyl-N-[(R)-α-methylbenzyl]amino}-4,4-diethoxybutanoate

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 2 h / -78 °C / Inert atmosphere

1.3: 12 h / -78 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / -20 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; methanol; hexane; dichloromethane; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation;
DOI:10.1016/j.tet.2014.03.055