(3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

Base Information

Chemical Name:(3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one
CAS No.:132094-22-5
Molecular Formula:C₁₈H₃₁NO₄
Molecular Weight:325.448
Hs Code.:

Synonyms:(3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

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Chemical Property of (3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

Chemical Property:

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Technology Process of (3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

There total 10 articles about (3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one 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:

: 112227-09-5
(5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

: 74-88-4
methyl iodide

: 132094-22-5
(3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

Guidance literature:: With lithium diisopropyl amide; Yield given. Multistep reaction; 1.) THF, -78 deg C;
DOI:10.1039/c39920001562

Reference yield:

: 21461-84-7
(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

: 132094-22-5
(3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / SOCl₂ / Heating

2: 52 percent / tetrahydrofuran / -78 °C

3: L-Selectride / tetrahydrofuran / -78 °C

4: 96 percent / Et₃N / CH₂Cl₂ / 0 °C

5: 71 percent / LiBr / tetrahydrofuran / Heating

6: 75 percent / NaN₃, DMPU / Ambient temperature

7: 89 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

8: 1.) LDA / 1.) THF, -78 deg C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; thionyl chloride; sodium azide; hydrogen; L-Selectride; triethylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1039/c39920001562

Reference yield:

: 54848-33-8
(S)-tetrahydro-5-oxo-2-furancarbonyl chloride

: 132094-22-5
(3R,5S,1'S)-5-(1'-tert-butoxycarbonylamino-2'-cyclohexylethyl)-3-methyldihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 7 steps

1: 52 percent / tetrahydrofuran / -78 °C

2: L-Selectride / tetrahydrofuran / -78 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 0 °C

4: 71 percent / LiBr / tetrahydrofuran / Heating

5: 75 percent / NaN₃, DMPU / Ambient temperature

6: 89 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

7: 1.) LDA / 1.) THF, -78 deg C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium azide; hydrogen; L-Selectride; triethylamine; lithium bromide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1039/c39920001562