(4R,5R)-Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Base Information

• Chemical Name: (4R,5R)-Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
• CAS No.: 59779-75-8
• Molecular Formula: C11H18 O6
• Molecular Weight: 246.26
• Hs Code.: 29329900
• DSSTox Substance ID: DTXSID30975191
• Nikkaji Number: J45.751E
• Wikidata: Q63409611
• Mol file: 59779-75-8.mol

Synonyms:59779-75-8;(4R,5R)-Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate;(4R,5R)-4,5-DIETHOXYCARBONYL-2,2-DIMETHYL DIOXOLANE;diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate;1,3-Dioxolane-4,5-dicarboxylic acid, 2,2-dimethyl-, diethyl ester,(4R,5R)-;Diethyl (R,R)-O,O-isopropylidenetartrate;SCHEMBL805599;DTXSID30975191;AS-76016;CS-0097519;D95613;2-AMINO-1-PYRIDIN-3-YL-ETHANONEHYDROCHLORIDE;Q63409611;(4R,5R)-Diethyl2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate;(4R,5R)-4,5-BIS(ETHOXYCARBONYL)-2,2-DIMETHYL-1,3-DIOXOLANE

Chemical Property of (4R,5R)-Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.00267mmHg at 25°C
• Refractive Index: 1.4345-1.4365
• Boiling Point: 92-93 °C
• Flash Point: 120.2°C
• PSA: 71.06000
• Density: 1.132g/cm³
• LogP: 0.63270
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 246.11033829
• Heavy Atom Count: 17
• Complexity: 270

Purity/Quality:

99% ^*data from raw suppliers

(4R,5R)-4,5-DIETHOXYCARBONYL-2,2-DIMETHYL DIOXOLANE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(OC(O1)(C)C)C(=O)OCC
• Isomeric SMILES: CCOC(=O)[C@H]1[C@@H](OC(O1)(C)C)C(=O)OCC

Technology Process of (4R,5R)-Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

There total 9 articles about (4R,5R)-Diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 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%

diethyl (2R,3R)-tartrate (87-91-2) + 2,2-dimethoxy-propane (77-76-9) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) + (4R,5R)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 8h; Title compound not separated from byproducts.; Heating;

DOI:10.1002/ejoc.200700449

Reference yield: 99.0%

diethyl (2R,3R)-tartrate (87-91-2) + acetone (67-64-1) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8)

Guidance literature:

With orthoformic acid triethyl ester;

DOI:10.1016/S0957-4166(01)00547-X

Reference yield: 98.0%

diethyl (2R,3R)-tartrate (87-91-2) + 2,2-dimethoxy-propane (77-76-9) → diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 8h; Heating;

DOI:10.1016/0040-4020(96)00792-2

upstream raw materials:

diethyl (2R,3R)-tartrate

acetone

Isopropyl acetate

2,2-dimethoxy-propane

Downstream raw materials:

(4R,5R)-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid 4,5-bis(N-benzylamide)

(R,R)-TADDOL

(4R,5R)-4-benzoyl-5--2,2-dimethyl-1,3-dioxolane

Refernces

• 1、 Yeager, Adam R.,Finney, Nathaniel S.. "Second-generation dimeric inhibitors of chitin synthase". . p. 6451 - 6460. Retrieved 2004.
• 2、 Fartade, Dipak J.,Gharpure, Santosh J.,Nanda, Santosh K.,Vishwakarma, Dharmendra S.. "Domino Hydroalkoxylation-[4+2]-Cycloaddition for Stereoselective Synthesis of 1,4-Heterocycle-Fused Chromenes: Rapid Access to the [6-6-7-6] Tetracyclic Core of Cytorhizhins B–D". supporting information. p. 6892 - 6897. Retrieved 2020/01/25.
• 3、 Sharma, Komal,Joseph, Jojo P.,Sahu, Adarsh,Yadav, Narender,Tyagi, Mohit,Singh, Ashmeet,Pal, Asish,Kartha, K.P. Ravindranathan. "Supramolecular gels from sugar-linked triazole amphiphiles for drug entrapment and release for topical application". . p. 19819 - 19827. Retrieved 2019/07/05.