(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Base Information

• Chemical Name: (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone
• CAS No.: 32384-42-2
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• Mol file: 32384-42-2.mol

Synonyms:(1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Chemical Property of (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

Chemical Property:

Purity/Quality:

99%min ^*data from raw suppliers

(3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3aR,4R,7S,8aR)-Tetrahydro-7-hydroxy-2,2-dimethyl-4,7-methano-1,3-dioxolo[4,5-c]oxepin-6(4H)-one is an intermediate used in the synthesis of 3-O-(E)-Feruloylquinic Acid (F308980), which is a phenolic acid with potential antioxidant and antifungal activities. Secondary metabolite in the coffee brewing process.

Technology Process of (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone

There total 15 articles about (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone 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%

D-(-)-quinic acid (77-95-2) + acetone (67-64-1) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Guidance literature:

With sulfuric acid; sodium sulfate; for 1h; Heating;

DOI:10.1016/j.carres.2003.10.026

Reference yield: 98.0%

D-(-)-quinic acid (77-95-2) + 2,2-dimethoxy-propane (77-76-9) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 1h; Reflux;

DOI:10.1016/j.tet.2015.02.092

Reference yield: 92.0%

2,2-dimethylpropane (463-82-1) + D-(-)-quinic acid (77-95-2) → (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone (32384-42-2)

Guidance literature:

With toluene-4-sulfonic acid; In ethyl acetate; at 0 - 78 ℃; for 12h;

DOI:10.1021/acs.orglett.7b00945

upstream raw materials:

D-(-)-quinic acid

quinamide

acetone

2,2-dimethoxy-propane

Downstream raw materials:

ethyl (3aR,5R,7R,7aS)-5,7-dihydroxy-2,2-dimethylhexahydro-benzo[1,3]dioxole-5-carboxylate

N-cyclohexyl 4,5-O-isopropylidene quinamide

(4S,5R)-4-hydroxy-5-propylcyclohex-2-enone

(2S,4S,5R)-4,5-dihydroxy-2-methyl cyclohexanone

Refernces

• 1、 Huang, Chih-Yu,Chen, Li-Hsun,Huang, Hsuan-Yu,Kao, Feng-Sheng,Lee, Yun-Ta,Selvaraju, Manikandan,Sun, Chung-Ming,Chen, Hueih-Min. "Parallel synthesis and biological evolution of quinic acid derivatives as immuno-suppressing agents against T-cell receptors". . p. 50801 - 50806. Retrieved 2015.
• 2、 Saito, Aki,Igarashi, Wataru,Furukawa, Hiroyuki,Yamada, Teiko,Kuwahara, Shigefumi,Kiyota, Hiromasa. "Facile synthesis of the cyclohexane fragment of enacloxins, a series of antibiotics isolated from Frateuria sp. W-315". . p. 766 - 769. Retrieved 2014.
• 3、 Gartman, Jackson A.,Tambar, Uttam K.. "Synthetic Studies of the Rubellin Natural Products: Development of a Stereoselective Strategy and Total Synthesis of (+)-Rubellin C". . p. 11237 - 11262. Retrieved 2021/08/16.
• 4、 Soklou, Kossi Efouako,Marzag, Hamid,Bouillon, Jean-Philippe,Marchivie, Mathieu,Routier, Sylvain,Plé, Karen. "Gold(I)-Catalyzed Intramolecular Hydroamination and Hydroalkoxylation of Alkynes: Access to Original Heterospirocycles". supporting information. p. 5973 - 5977. Retrieved 2020/08/12.