Cyclooctanone, 2,3-dihydroxy-, (2R,3R)-rel- (9CI)

Base Information

• Chemical Name: Cyclooctanone, 2,3-dihydroxy-, (2R,3R)-rel- (9CI)
• CAS No.: 664987-32-0
• Molecular Formula: C8H14O3
• Molecular Weight: 158.2
• Mol file: 664987-32-0.mol

Synonyms:Cyclooctanone, 2,3-dihydroxy-, (2R,3R)-rel- (9CI)

Chemical Property of Cyclooctanone, 2,3-dihydroxy-, (2R,3R)-rel- (9CI)

Chemical Property:

• PSA: 57.53000
• LogP: 0.24140

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclooctanone, 2,3-dihydroxy-, (2R,3R)-rel- (9CI)

There total 21 articles about Cyclooctanone, 2,3-dihydroxy-, (2R,3R)-rel- (9CI) 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%

cis-3-benzyloxy-2-hydroxycyclooctanone → cis-2,3-dihydroxycyclooctanone (664987-32-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 760 Torr;

DOI:10.1021/jo0358675

Reference yield: 93%

cis-3-(tert-butyldimethylsilyloxy)-2-hydroxycyclooctanone → cis-2,3-dihydroxycyclooctanone (664987-32-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 0.5h;

DOI:10.1021/jo0358675

Reference yield: 90%

(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-cyclooctanone → (2S,3S)-2,3-dihydroxycyclooctanone (664987-32-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1002/adsc.200404002

upstream raw materials:

2-hydroxycylooctanone

2-(benzyloxy)cyclooctanone

3-benzyloxy-1,2-cyclooctanedione

3-(tert-butyl-dimethyl-silanyloxy)-cyclooctane-1,2-dione

Downstream raw materials:

(1S,2R)-Cyclooctane-1,2,3-triol

cyclooctane-1,2,3-triol

cyclooctane-1,2,3-triol

Refernces

• 1、 Hartung, Ryan E.,Hilmey, David G.,Paquette, Leo A.. "Fluoride ion-promoted α-ketol rearrangement during unmasking of silyl-protected medium-ring dihydroxy ketones". . p. 713 - 716. Retrieved 2007/10/03.
• 2、 Paquette, Leo A.,Hartung, Ryan. "Chemical consequences of the ground-state conformations of cyclooctyl rings. Examples of reactivity differences in α-hydroxy and α,α′-dihydroxy eight-membered cyclic ketones". . p. 1201 - 1208. Retrieved 2007/10/03.