143308-74-1

Basic information

• Product Name: (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-diMethyl-1,3-benzodioxole-5-carboxylic Acid Methyl Ester
• Synonyms: (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-diMethyl-1,3-benzodioxole-5-carboxylic Acid Methyl Ester;3,4-(Isopropylidenedioxy) ShikiMic Acid Methyl Ester Acetate
• CAS NO: 143308-74-1
• Molecular Formula: C₁₃H₁₈O₆
• Molecular Weight: 270.27842
• Product Categories: Chiral Reagents;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals;Chiral Reagents, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 143308-74-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly, Sonicated)
• CAS DataBase Reference: (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-diMethyl-1,3-benzodioxole-5-carboxylic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-diMethyl-1,3-benzodioxole-5-carboxylic Acid Methyl Ester(143308-74-1)
• EPA Substance Registry System: (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-diMethyl-1,3-benzodioxole-5-carboxylic Acid Methyl Ester(143308-74-1)

Safety Data

• Hazardous Substances Data: 143308-74-1(Hazardous Substances Data)

Usage

Description

(3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-5-carboxylic acid methyl ester is a complex organic compound derived from shikimic acid, characterized by its pale yellow solid appearance. It features a unique molecular structure with a benzodioxole core, multiple stereocenters, and functional groups such as an acetyloxy group and a methyl ester.

Uses

Used in Pharmaceutical Industry:
(3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-5-carboxylic acid methyl ester is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and functional groups make it a valuable building block for the development of new drugs, particularly those targeting specific biological pathways.
Used in Chemical Research:
As a complex organic molecule, (3R,4S,5R)-7-(Acetyloxy)-3a,6,7,7a-tetrahydro-2,2-dimethyl-1,3-benzodioxole-5-carboxylic acid methyl ester is also used in chemical research for studying reaction mechanisms, stereochemistry, and the synthesis of novel compounds with potential applications in various fields.
Used in Material Science:
The compound's unique structure and properties may also find applications in material science, potentially serving as a component in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity in various chemical processes.

Upstream product

• 88165-26-8 methyl 3,4-O-isopropylideneshikimate 
• 108-24-7 acetic anhydride 
• 91766-49-3 (+/-)-2t,5t-diacetoxy-3c,4c-dihydroxy-cyclohexane-r-carboxylic acid methyl ester 
• 92490-01-2 1β,4β-Diacetoxy-5α-carbomethoxy-2-cyclohexene 
• 261631-95-2 (-)-(1S)-1-{(4S,5S)-5-[(1S)-1-hydroxy-2-propenyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propen-1-ol 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 1121652-18-3 (3aS,5aS,6aS,6bS)-2,2-dimethyl-3a,5a,6a,6b-tetrahydrooxireno-[2′,3′:3,4]benzo[1,2-d][1,3]dioxole 
• 1582806-01-6 (3aR,4S,7R,7aS)-methyl 4,7-dihydroxy-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 1582806-00-5 (3aR,4S,5S,5aR,6aR,6bS)-methyl 4-hydroxy-2,2-dimethylhexahydrooxireno[2′,3′:3,4]benzo[1,2-d][1,3]dioxole-5-carboxylate 
• 1582805-99-9 (3aR,4S,5R,7aS)-methyl 4-hydroxy-2,2-dimethyl-3a,4,5,7atetrahydrobenzo[d][1,3]dioxole-5-carboxylate 
• 146582-76-5 Acetic acid (3aR,4R,7R,7aS)-7-acetoxy-5-furan-2-yl-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-4-yl ester 
• 146582-74-3 Acetic acid (3aS,4R,7R,7aR)-6-furan-2-yl-7-hydroxy-2,2-dimethyl-3a,4,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl ester 
• 1052649-85-0 (3aR,4R,7R,7aS)-4,7-Diacetoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid 
• 146582-73-2 (-)-7-Acetoxy-5-(2-furyl)-3aα,4,7α,7aα-tetrahydro-2,2-dimethyl-1,3-benzodioxol-4-one 

Downstream Products

• 1104200-21-6 (1S)-3t-acetoxy-4c,5c-dihydroxy-cyclohexane-r-carboxylic acid methyl ester 
• 93060-75-4 (-)-shikimate 3-phosphate trisodium salt 
• 352533-33-6 methyl (3S,4R,5R)-3-acetamido-5-acetoxy-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 352533-31-4 methyl (3S,4R,5R)-5-acetoxy-3-azido-4-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate 
• 352533-37-0 methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-azidocyclohex-1-ene-1-carboxylate 
• 352533-39-2 methyl (3R,4S,5R)-4-acetamido-5-acetoxy-3-aminocyclohex-1-ene-1-carboxylate 
• 352533-29-0 methyl (3S,4R,5R)-5-acetoxy-3-azido-4-hydroxycyclohex-1-ene-1-carboxylate 
• 76947-24-5 Methyl 5-O-Acetyl-(-)-shikimate 
• 40983-58-2 methyl shikimate 
• 15271-51-9 (+/-)-shikimic acid 

Relevant articles and documents

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Synthesis of a carbocyclic sialic acid analogue for the inhibition of influenza virus neuraminidase

The influenza virus neuraminidase (NA) is essential for viral infection and offers a potential target for antiviral drug development. We prepared a carbocyclic sialic acid analogue, potentially able to inhibit NA. Its structure is an analogue of the trans

Synthesis of (+)- and (-)-Methyl Shikimate from Benzene

cis-Cyclohexa-3,5-diene-1,2-diol 2, the product of oxidation of benzene by mutants of Pseudomonas putida, was transformed into optically pure 4 in a sequence involving asymmetrization of meso-diol 3 in organic media with Pseudomonas cepacia lipase.Alcohol