[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Base Information

Chemical Name:[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester
CAS No.:674787-19-0
Molecular Formula:C₂₃H₂₅NO₄
Molecular Weight:379.456
Hs Code.:

Synonyms:[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

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Chemical Property of [(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Chemical Property:

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Technology Process of [(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

There total 1 articles about [(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 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:

: 556-56-9
allyl iodid

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

: [(S)-1-((2S,4S)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

: 674787-19-0
[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

: [(S)-1-((S)-4,4-Diallyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/j.bmcl.2003.11.061

Reference yield: 73.0%

: 674787-19-0
[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

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

Guidance literature:: [(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester; With 3>; benzo[1,3,2]dioxaborole; In tetrahydrofuran; at 20 ℃; for 1.5h;

With potassium dihydrogenphosphate; dihydrogen peroxide; In tetrahydrofuran; ethanol; at 20 ℃; for 12h; pH=7.2;
DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

: 674787-19-0
[(S)-1-((2S,4R)-4-Allyl-5-oxo-tetrahydro-furan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

: (4R,6S,7S)-7-[(S)-3-Carboxy-3-(3-methyl-butyrylamino)-propionylamino]-6-hydroxy-4-isobutylcarbamoyl-8-phenyl-octanoic acid

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: 73 percent / aq. H₂O₂; KH₂PO₄ / tetrahydrofuran; ethanol / 12 h / 20 °C / pH 7.2

2.1: 76 percent / aq. NaIO₄; RuCl₃ / acetonitrile; CCl₄ / 2 h

3.1: 50 percent / H₂SO₄ / CH₂Cl₂; dioxane / 48 h

4.1: 2-hydroxypyridin / 72 h

5.1: H₂ / Pd/C / ethanol / 2 h

6.1: EDT; HOBt; NMM / dimethylformamide / 20 h

7.1: piperidine / dimethylformamide / 0.17 h

8.1: EDT; HOBt; NMM / dimethylformamide / 20 h

9.1: TFA

With piperidine; 4-methyl-morpholine; 2-hydroxypyridin; ruthenium trichloride; sodium periodate; 3>; ethylenediaminetetraacetic acid; sulfuric acid; hydrogen; benzotriazol-1-ol; trifluoroacetic acid; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Sharpless oxidation;
DOI:10.1016/j.bmcl.2003.11.061