{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

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Chemical Name:{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester
CAS No.:333405-32-6
Molecular Formula:C₂₀H₂₉NO₅
Molecular Weight:363.454
Hs Code.:

Synonyms:{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

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Chemical Property of {(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

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Technology Process of {(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

There total 2 articles about {(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl 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: 73.0%

: 137281-77-7
{(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

: 333405-32-6
{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

Guidance literature:: {(1S)-1-[(4R)-4-allyl-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl 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:

: 133333-27-4
tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate

: 333405-32-6
{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 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

With 3>; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran;
DOI:10.1016/j.bmcl.2003.11.061

Reference yield:

: 333405-32-6
{(1S)-1-[(4R)-4-(3-hydroxy-propyl)-5-oxo-tetrahydro-furan-(2S)-2-yl]-2-phenyl-ethyl} carbamic acid tert-butyl ester

: C₄₄H₄₆N₄O₅H₂SiH₁₂CN₂(C₅H₈O₂)2

Guidance literature:: Multi-step reaction with 8 steps

1: triethylamine / toluene / 0 - 20 °C

2: NaN₃; Bu₄NBr / H₂O; toluene / 3 h / Heating

3: aq. HCl / dioxane; tetrahydrofuran / 1 h / 20 °C

4: HOBT; EDCI; DIEA / dimethylformamide / 0 - 20 °C

5: aq. LiOH / dioxane / 20 °C

6: 0.093 g / imidazole / dimethylformamide / 44 h / 20 °C

7: 62 percent / PPh₃; aq. LiOH / H₂O; tetrahydrofuran / 48 h / 20 °C

8: H₂ / Pd(OH)2/C / methanol / 6 h / 760.05 Torr

With 1H-imidazole; hydrogenchloride; lithium hydroxide; sodium azide; tetrabutylammomium bromide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; toluene; 7: Staudinger reaction;
DOI:10.1021/ol015612i