(1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate

Base Information

• Chemical Name: (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate
• CAS No.: 863224-35-5
• Molecular Formula: C₁₆H₂₂O₁₀
• Molecular Weight: 374.345
• Mol file: 863224-35-5.mol

Synonyms:(1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate

Chemical Property of (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate

There total 10 articles about (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 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: 45.0%

(1R,2R,3R,4R,5S)-3,4-epoxy-1,2-O-cyclohexylidene-1,2,5-trihydroxycyclohexane + acetic anhydride (108-24-7) → (1R,2R,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate (20097-36-3) + (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate (863224-35-5)

Guidance literature:

With sulfuric acid; Heating;

DOI:10.1081/SCC-200063960

Reference yield:

(1S,2S,4R)-cyclohex-5-ene-1,2,4-triyl triacetate + acetic anhydride (108-24-7) → (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate (863224-35-5) + rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate (68907-51-7)

Guidance literature:

(1S,2S,4R)-cyclohex-5-ene-1,2,4-triyl triacetate; With benzenesulfonamide; potassium osmate(VI) dihydrate; sodium hydrogencarbonate; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; potassium hexacyanoferrate(III); In water; tert-butyl alcohol; at 0 ℃; for 120h;

acetic anhydride; In dichloromethane; water; tert-butyl alcohol; at 20 ℃; for 15h;

DOI:10.1055/s-0034-1379603

Reference yield:

C17H20O5 → (1R,2R,3S,4R,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate (863224-35-5) + rac-(1R,2S,3S,4R,5S)-cyclohexane 1,2,3,4,5-pentaylpentaacetate (68907-51-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dmap

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / water; dichloromethane / 72 h / 20 °C

3.1: dmap; pyridine / dichloromethane / 2 h / 20 °C

4.1: sodium tetrahydroborate / methanol / 0.75 h / -20 °C

5.1: dmap; pyridine / dichloromethane / 6 h / 20 °C

6.1: potassium osmate(VI) dihydrate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; benzenesulfonamide; potassium hexacyanoferrate(III); potassium carbonate; sodium hydrogencarbonate / water; tert-butyl alcohol / 120 h / 0 °C

6.2: 15 h / 20 °C

With pyridine; benzenesulfonamide; dmap; potassium osmate(VI) dihydrate; sodium tetrahydroborate; sodium hydrogencarbonate; potassium carbonate; 4-[(R)-[(2R,4R,5S)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]-1-[(R)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxy-4-quinolinyl)methoxy]phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); In methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1055/s-0034-1379603

upstream raw materials:

acetic anhydride

Downstream raw materials:

(+)-2-deoxy-epi-inositol