32384-42-2

Basic information

• Product Name: (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone
• Synonyms: (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone
• CAS NO: 32384-42-2
• Molecular Weight: 214.218
• Mol File: 32384-42-2.mol
• Article Data: 44

Chemical Properties

• CAS DataBase Reference: (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone(32384-42-2)
• EPA Substance Registry System: (1S,3R,4S,5R)-3,4-O-isopropylidene-1,5-quinic lactone(32384-42-2)

Safety Data

• Hazardous Substances Data: 32384-42-2(Hazardous Substances Data)

Usage

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.

Upstream product

• 77-95-2 D-(-)-quinic acid 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 77-76-9 2,2-dimethoxy-propane 
• 463-82-1 2,2-dimethylpropane 
• 191916-39-9 methyl (-)-quinate 
• 364628-95-5 Trimethylsilyltetra-O-trimethylsilylchinat 
• 67-64-1 acetone 
• 78579-44-9 quinamide 

Downstream Products

• 612819-77-9 N-benzyl 4,5-O-isopropylidene quinamide 
• 874473-01-5 N-cyclohexyl 4,5-O-isopropylidene quinamide 
• 244231-01-4 (3S,4R,5R)-3-(tert-Butyl-diphenyl-silanyloxy)-4,5-dihydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 205932-30-5 Benzoic acid (3aS,4aR,7aS,8R,8aS)-8-hydroxy-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester 
• 205932-31-6 Toluene-4-sulfonic acid (3aS,4aR,7aS,8R,8aS)-8-hydroxy-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester 
• 199338-66-4 Benzoic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester 
• 199338-67-5 Toluene-4-sulfonic acid (3aS,4aR,7aR,8R,8aS)-8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-ylmethyl ester 
• 244230-73-7 (3aR,4aR,7aR,8aR)-7a-(Hydroxy-diphenyl-methyl)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-one 
• 244230-94-2 (3aS,4R,4aS,7aR,8aR)-7a-(Hydroxy-diphenyl-methyl)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol 
• 244231-02-5 (3aR,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 244230-93-1 [8-(tert-butyl-dimethyl-silanyloxy)-2,2,6,6-tetramethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-3a-yl]-diphenyl-methanol 
• 244231-03-6 (3aR,5R,6S,7S,7aR)-7-(tert-Butyl-diphenyl-silanyloxy)-2,2-diethyl-5,6-dihydroxy-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 244231-04-7 8-(tert-butyl-diphenyl-silanyloxy)-6,6-diethyl-2,2-dimethyl-tetrahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxole-3a-carboxylic acid methyl ester 
• 1257059-73-6 1-O-benzyl-3,4-O-isopropylidene-1,5-quinic lactone 

Relevant articles and documents

[2+2] Photoadditions with chiral 2,5-cyclohexadienone synthons

Three chiral 2,5-cyclohexadienone synthons bearing different chiral auxiliaries were examined in [2+2] photoadditions with cyclopentene. Regeneration of the 'masked' double bond in the adducts resulted in the preparation of optically active 5-4-6 adducts. The enantiomeric purity of each adduct was found to be >95% using comparative 13C NMR analysis of the appropriate ketals. The asymmetry induced in the cycloaddition step of our methodology indicated that the facial selectivity was directly correlated to the degree of steric bulk of the chiral auxiliary on the synthon.

Asymmetric Total Synthesis of (-)-Guignardones A and B

The asymmetric total synthesis of (-)-guignardones A (2) and B (1) has been accomplished. The highly oxidized 6-oxabicyclo[3.2.1]octane core was constructed from d-quinic acid via substitution/desulfurization reaction with thiophenol to forge the bridged ring scaffold, and a Pummerer rearrangement and 1,4-addition/elimination sequence was employed to install the β-carbonyl group at the congested C-1 position. A late-stage Knoevenagel condensation-6π-electrocyclization and directed hydrogenation formed (-)-guignardone B (1), which was subjected to dehydration to furnish (-)-guignardone A (2).

Total syntheses of aminomethyl-C-dideoxyglycopyranosides and their quinamides

Lewis acid promoted cyclization of homoallylic alcohol 1 with acetal 2 gave 4-chloro-2-phthalimidomethyl-6-methyltetrahydropyrans. Their dehydrochlorination produced two regioisomeric dihydropyrans. Subsequent cis- and trans-dihydroxylation gave four race

Sulfamate-tethered aza-Wacker approach towards analogs of Bactobolin A

Here, we describe an approach towards analogs of the potent antibiotic Bactobolin A. Sulfamate-tethered aza-Wacker cyclization reactions furnish key synthons, which we envision can be elaborated into analogs of Bactobolin A. Docking studies show that the

A concise synthesis of carbasugars isolated from Streptomyces lincolnensis

(?)-Quinic acid was used as a starting material in the hemisynthesis of two epimeric carbasugars isolated from Streptomyces lincolnensis. Previous 10–12 steps syntheses for the carbasugars have been herein shortened to 4–6 steps by using quinic acid as a