(3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one
• CAS No.: 124032-36-6
• Molecular Formula: C₂₀H₃₅NO₄
• Molecular Weight: 353.502
• Mol file: 124032-36-6.mol

Synonyms:(3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one

Chemical Property of (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one

There total 26 articles about (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-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: 99.0%

monomethyl oxalyl chloride (5781-53-3) + (3S,5S)-5-[(1S)-1-(N-t-butoxycarbonylamino)-2-cyclohexylethyl]-3-(1-hydroxy-1-methylethyl)dihydrofuran-2(3H)-one (125015-95-4) → (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one (124032-36-6)

Guidance literature:

With dmap; sodium chloride; azobisisobutyronitrile; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; toluene;

Reference yield: 76.0%

Oxalic acid 1-[(3S,5S)-5-((S)-1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-1-methyl-ethyl ester methyl ester (127772-94-5) → (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one (124032-36-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; Heating;

Reference yield:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal (98105-42-1) → (3S,5S)-5-[(1S)-1-(t-butoxycarbonyl)amino-2-cyclohexylethyl]-3-isopropyldihydrofuran-2(3H)-one (124032-36-6)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / -78 °C

2: H₂ / Pd/BaSO₄ / ethyl acetate / 3040 Torr

3: PCC, molecular sieves (3 Angstroem) / CH₂Cl₂

4: 1.) KBH₄, 2.) HOAc / 1.) ethanol, 0 deg C, 6 h, 2.) toluene, reflux

5: 1) LDA / 2) THF, -78 deg C

6: 99 percent / NEt₃, DMAP / tetrahydrofuran / 0 °C

7: 76 percent / n-Bu₃SnH, AIBN / toluene / Heating

With dmap; potassium borohydride; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; hydrogen; tri-n-butyl-tin hydride; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; Pd-BaSO₄; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;

upstream raw materials:

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

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

Oxalic acid 1-[(3S,5S)-5-((S)-1-tert-butoxycarbonylamino-2-cyclohexyl-ethyl)-2-oxo-tetrahydro-furan-3-yl]-1-methyl-ethyl ester methyl ester

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

Downstream raw materials:

(2S,3S,5S)-2-tert-butyloxycarbonylamino-1-cyclohexyl-5-isopropylhexan-3,6-diol

(2S,4S,5S)-5-(t-butoxycarbonyl)amino-6-cyclohexyl-4-hydroxy-2-isopropyl-N-butylhexanamide

[(1S,2S,4S)-1-Cyclohexylmethyl-2-hydroxy-5-methyl-4-(2-morpholin-4-yl-ethylcarbamoyl)-hexyl]-carbamic acid tert-butyl ester

[(1S,2S,4S)-1-Cyclohexylmethyl-2-hydroxy-4-(3-imidazol-1-yl-propylcarbamoyl)-5-methyl-hexyl]-carbamic acid tert-butyl ester