(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

Base Information

Chemical Name:(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid
CAS No.:286939-12-6
Molecular Formula:C₁₇H₂₆N₂O₅
Molecular Weight:338.404
Hs Code.:

Synonyms:(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

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Chemical Property of (2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

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Technology Process of (2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

There total 4 articles about (2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid 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: 96.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 286939-11-5
(2S,3S)-3-((benzyloxy)amino)-2-((tert-butoxycarbonyl)amino)butanoic acid

: 286939-12-6
(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

Guidance literature:: With sodium cyanoborohydride; In methanol; water; at 20 ℃; for 4h;
DOI:10.1021/ja003292c

Reference yield:

: 75659-16-4
(3S-trans)-3-[(t-Butyloxycarbonyl)amino]-4-methyl-2-oxo-1-(phenylmethoxy)azetidine

: 286939-12-6
(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / aq. NaOH / dioxane / 2.5 h / 20 °C

2: 96 percent / NaCNBH₃ / methanol; H₂O / 4 h / 20 °C

With sodium hydroxide; sodium cyanoborohydride; In 1,4-dioxane; methanol; water;
DOI:10.1021/ja003292c

Reference yield:

: 2592-18-9
Boc-Thr-OH

: 286939-12-6
(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-[(N-benzyloxy-N-methyl)amino]butanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / acetonitrile / 0.17 h / 20 °C / Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 22 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydroxide / tetrahydrofuran; water / 2.25 h / 20 °C / Inert atmosphere

4.1: sodium cyanoborohydride / methanol; water / 4 h / 0 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; sodium cyanoborohydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1021/acs.jmedchem.1c01407