3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

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Chemical Name:3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid
CAS No.:674787-23-6
Molecular Formula:C₂₃H₂₅NO₆
Molecular Weight:411.455
Hs Code.:

Synonyms:3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

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Chemical Property of 3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

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Technology Process of 3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

There total 2 articles about 3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic 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: 76.0%

: 674787-20-3
{(S)-1-[(2S,4R)-4-(3-Hydroxy-propyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid benzyl ester

: 674787-23-6
3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; for 2h;
DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

: 143601-50-7
phenylmethyl [(1S)-2-phenyl-1-[(2S)-tetrahydro-5-oxo-2-furanyl]ethyl]carbamate

: 674787-23-6
3-[(3R,5S)-5-((S)-1-Benzyloxycarbonylamino-2-phenyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-propionic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.1: Rh(PPh₃)3; catechol borane / tetrahydrofuran / 1.5 h / 20 °C

2.2: 73 percent / aq. H₂O₂; KH₂PO₄ / tetrahydrofuran; ethanol / 12 h / 20 °C / pH 7.2

3.1: 76 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 2 h

With ruthenium trichloride; sodium periodate; 3>; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; tetrachloromethane; acetonitrile; 3.1: Sharpless oxidation;
DOI:10.1016/j.bmcl.2003.11.061