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

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

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

• 19902-87-5 (3aR,4R,7R,7aS)-4,7-Diacetoxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid methyl ester 
• 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 
• 19902-87-5 (+/-)-4c,7c-diacetoxy-2,2-dimethyl-(3ar,7ac)-hexahydro-benzo[1,3]dioxole-5t-carboxylic acid methyl ester 
• 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 
• 108-24-7 acetic anhydride 
• 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 

Downstream Products

• 40983-58-2 methyl shikimate 
• 76947-24-5 Methyl 5-O-Acetyl-(-)-shikimate 
• 15271-51-9 (+/-)-shikimic acid 
• 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 

Relevant articles and documents

A C 2-symmetric chiral pool-based flexible strategy: Synthesis of (+)- and (-)-shikimic acids, (+)- and (-)-4- epi -shikimic acids, and (+)- and (-)-pinitol

Via combination of a novel acid-promoted rearrangement of acetal functionality with the controlled installation of the epoxide unit to create the pivotal epoxide intermediates in enantiomerically pure form, a simple, concise, flexible, and readily scalable enantiodivergent synthesis of (+)- and (-)-shikimic acids and (+)- and (-)-4-epi-shikimic acids has emerged. This simple strategy not only provides an efficient approach to shikimic acids but also can readily be adopted for the synthesis of (+)- and (-)-pinitols. These concise total syntheses exemplify the use of pivotal allylic epoxide 14 and its enantiomer ent-14. A readily available inexpensive C2-symmetric l-tartaric acid (7) served as key precursor. In general, the strategy here provides a neat example of the use of a four-carbon chiron and offers a good account of the synthesis of functionalized cyclohexane targets.

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 and activity of C2-substituted analogs of influenza neuraminidase inhibitor GS 4071

The influence of C2-substitution of GS 4071 on the influenza neuraminidase inhibitory activity was investigated. The introduction of lipophilic substituents (chloro, methyl, and methylthio) at the C2 position resulted in a significant decrease of the activity. This result indicates that at the enzyme active site there is limited hydrophobic pocket for a group at the C2 position of GS 4071.

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