(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

Base Information

Chemical Name:(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol
CAS No.:872033-11-9
Molecular Formula:C₁₉H₃₀N₂O₄
Molecular Weight:350.458
Hs Code.:

Synonyms:(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

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Chemical Property of (1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

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Technology Process of (1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

There total 4 articles about (1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol 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: 95.0%

: 872033-10-8
(2S,3S,4R,5R)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-4,5-epoxy-3-hydroxy-1-phenyloctane

: 872033-11-9
(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

Guidance literature:: With hydrogen; 5% palladium-on-charcoal; In methanol; for 16h;

Reference yield:

: 872033-26-6
(E,2S)-8-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)-3-oxo-1-phenyloct-4-ene

: 872033-11-9
(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1: lithium tri-t-butoxyaluminum hydride / ethanol / -78 - -60 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

3: palladium on activated charcoal; hydrogen / methanol / 16 h / 25 °C

With palladium on activated charcoal; hydrogen; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; In methanol; ethanol; dichloromethane;
DOI:10.1021/jm3001136

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 872033-11-9
(1S,2S,3S)-3-tert-butoxycarbonylamino-4-phenyl-1-((S)-pyrrolidin-2-yl)butane-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.25 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - -30 °C / Inert atmosphere

2.1: potassium carbonate / acetonitrile / 0.25 h / 25 °C / Inert atmosphere

2.2: 48 h

3.1: lithium tri-t-butoxyaluminum hydride / ethanol / -78 - -60 °C / Inert atmosphere

4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 16 h / 0 - 20 °C

5.1: palladium on activated charcoal; hydrogen / methanol / 16 h / 25 °C

With n-butyllithium; palladium on activated charcoal; hydrogen; potassium carbonate; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; acetonitrile; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jm3001136