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

Base Information

• Chemical Name: (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one
• CAS No.: 112227-09-5
• Molecular Formula: C₁₇H₂₉NO₄
• Molecular Weight: 311.422
• Mol file: 112227-09-5.mol

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

Chemical Property of (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one

There total 23 articles about (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (5S,1'S)-5-(1'-azido-2'-cyclohexylethyl)dihydrofuran-2(3H)-one (125218-53-3) → (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one (112227-09-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/0040-4039(91)80024-Z

Reference yield:

tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate (133333-27-4) → (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one (112227-09-5)

Guidance literature:

In methanol;

Reference yield:

(S)-tetrahydro-5-oxo-2-furancarbonyl chloride (54848-33-8) → (5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]dihydrofuran-2(3H)-one (112227-09-5)

Guidance literature:

Multi-step reaction with 6 steps

1: tetrahydrofuran / 0.5 h / -78 °C

2: 91 percent / lithium tri-sec-butylborohydride (L-Selectride) / tetrahydrofuran / 0.5 h / -78 °C

3: 96 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: 71 percent / LiBr / tetrahydrofuran / 8 h / Heating

5: 75 percent / NaN₃, N,N'-dimethylpropyleneurea (DMPU) / 120 h / Ambient temperature

6: 89 percent / H₂ / 10percent Pd/C / ethyl acetate / 3 h / Ambient temperature

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

DOI:10.1248/cpb.41.1378

upstream raw materials:

di-tert-butyl dicarbonate

(5S,1'S)-5-(1'-azido-2'-cyclohexylethyl)dihydrofuran-2(3H)-one

(S)-5-tert-Butoxycarbonylamino-6-cyclohexyl-4-oxo-hexanoic acid ethyl ester

(S)-4-Cyclohexylmethyl-5-formyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

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

2S,4S,5S-6-Cyclohexyl-5-(t-butoxycarbonylamino)-2-(2-methyl-2-propenyl)-gamma-hexanolactone

2R,4S,5S-6-cyclohexyl-5-(t-butoxycarbonylamino)-2-(2'-methyl-2'-propenyl)-gamma-hexanolactone

[(S)-2-Cyclohexyl-1-((2S,4R)-4-isopropyl-5-oxo-tetrahydro-furan-2-yl)-ethyl]-carbamic acid tert-butyl ester