(2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

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Chemical Name:(2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid
CAS No.:1309572-04-0
Molecular Formula:C₁₉H₃₁NO₆
Molecular Weight:371.442
Hs Code.:

Synonyms:(2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

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Chemical Property of (2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

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Technology Process of (2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

There total 10 articles about (2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic 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:

: C₂₆H₃₅NO₅

: 1309572-04-0
(2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / hexane; toluene / 2 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C

2.1: chromium dichloride; sodium iodide / tetrahydrofuran / 20 °C / Inert atmosphere

3.1: Grubbs catalyst first generation / dichloromethane / 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran

6.1: dipyridinium dichromate

With Grubbs catalyst first generation; chromium dichloride; dipyridinium dichromate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium iodide; In tetrahydrofuran; hexane; dichloromethane; toluene; 2.1: Nozaki-Hiyama-Kishi reaction;
DOI:10.1021/ol201120k

Reference yield:

: (E)-2,3-dideuteroocta-2,7-dien-1-ol

: 1309572-04-0
(2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

2: chromium dichloride; sodium iodide / tetrahydrofuran / 20 °C / Inert atmosphere

3: Grubbs catalyst first generation / dichloromethane / 20 °C / Inert atmosphere

4: pyridinium p-toluenesulfonate / dichloromethane / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran

6: dipyridinium dichromate

With pyridine; Grubbs catalyst first generation; chromium dichloride; dmap; dipyridinium dichromate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium iodide; In tetrahydrofuran; dichloromethane; 2: Nozaki-Hiyama-Kishi reaction;
DOI:10.1021/ol201120k

Reference yield:

: 1309572-11-9
tert-butyl (1S,2S)-3-(tert-butyldiphenylsilyloxy)-1-((S)-1,2-dideuterocyclohex-2-enyl)-1-(tetrahydro-2H-pyran-2-yloxy)propan-2-ylcarbamate

: 1309572-04-0
(2R,3S)-2-(tert-butoxycarbonylamino)-3-((S)-1,2-dideuterocyclohex-2-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)propanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran

2: dipyridinium dichromate

With dipyridinium dichromate; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ol201120k