(5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one
• CAS No.: 137530-19-9
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.289
• Mol file: 137530-19-9.mol

Synonyms:(5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one

Chemical Property of (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one

There total 4 articles about (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)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: 91.0%

(S)-5-(2'-cyclohexyl-1'-oxoethyl)dihydrofuran-2(3H)-one (137530-18-8) → (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one (137530-19-9)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1248/cpb.41.1378

Reference yield:

(S)-5-(2'-cyclohexyl-1'-oxoethyl)dihydrofuran-2(3H)-one (137530-18-8) → (S)-5-((R)-2-Cyclohexyl-1-hydroxy-ethyl)-dihydro-furan-2-one (136944-72-4) + (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one (137530-19-9)

Guidance literature:

With sodium tetrahydroborate; Yield given. Yields of byproduct given;

DOI:10.1039/c39920001562

Reference yield:

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (5S,1'S)-5-(2'-cyclohexyl-1'-hydroxyethyl)dihydrofuran-2(3H)-one (137530-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / SOCl₂ / 2 h / Heating

2: tetrahydrofuran / 0.5 h / -78 °C

3: 91 percent / lithium tri-sec-butylborohydride (L-Selectride) / tetrahydrofuran / 0.5 h / -78 °C

With thionyl chloride; L-Selectride; In tetrahydrofuran;

DOI:10.1248/cpb.41.1378

upstream raw materials:

(S)-5-(2'-cyclohexyl-1'-oxoethyl)dihydrofuran-2(3H)-one

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

(S)-tetrahydro-5-oxo-2-furancarbonyl chloride

Downstream raw materials:

(5S,1'S)-5-(2'-cyclohexyl-1'-methanesulfonyloxyethyl)dihydrofuran-2(3H)-one

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

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

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