(+)-Diisopropyl L-tartrate

Base Information

• Chemical Name: (+)-Diisopropyl L-tartrate
• CAS No.: 2217-15-4
• Deprecated CAS: 4055-05-4,91007-92-0,116654-05-8,1427677-03-9
• Molecular Formula: C10H18O6
• Molecular Weight: 234.249
• Hs Code.: 29181300
• European Community (EC) Number: 218-709-0
• UNII: 7Z907X7UEY
• DSSTox Substance ID: DTXSID401030983
• Nikkaji Number: J130.113F
• Wikipedia: Diisopropyl_tartrate
• Wikidata: Q83080763
• Mol file: 2217-15-4.mol

Synonyms:2217-15-4;(+)-Diisopropyl L-tartrate;(2R,3R)-Diisopropyl 2,3-dihydroxysuccinate;Diisopropyl L-(+)-Tartrate;(+)-DIPT;Di-isopropyl tartrate;L-DIPT;L-(+)-Tartaric acid diisopropyl ester;diisopropyl (+)-tartrate;diisopropyl l-tartrate;dipropan-2-yl (2R,3R)-2,3-dihydroxybutanedioate;Diisopropyl (+)-L-tartrate;AI3-03572;7Z907X7UEY;Tartaric acid, diisopropyl ester;DIISOPROPYL (2R,3R)-2,3-DIHYDROXYSUCCINATE;EINECS 218-709-0;(+)-Tartaric acid diisopropyl ester;BRN 1727863;Butanedioic acid, 2,3-dihydroxy-, bis(1-methylethyl) ester, (R*,R*)-;Butanedioic acid, 2,3-dihydroxy-, bis(1-methylethyl) ester, (R,R)-(+/-)-;2-03-00-00331 (Beilstein Handbook Reference);58167-01-4;MFCD00064450;Butanedioic acid, 2,3-dihydroxy- (R-(R*,R*))-, bis(1-methylethyl) ester;Butanedioic acid, 2,3-dihydroxy- [R-(R*,R*)]-, bis(1-methylethyl) ester;L-(+)-Diisopropyl-tartrate, L-DIPT;Diisoprropyl L-tartrate;(+)diisopropyl L-tartrate;(R,R)-diisopropyl tartrate;Diisopropyl (R,R)-tartrate;UNII-7Z907X7UEY;(R,R) -diisopropyl tartrate;SCHEMBL1338978;DTXSID401030983;AKOS016843654;NSC 406502;Tartaric acid, diisopropyl ester, ()-;AC-19182;AC-20452;AM200001;AS-11874;CS-0010100;T0621;EN300-63837;Q-200004;Z991121796;1,4-bis(propan-2-yl) (2R,3R)-2,3-dihydroxybutanedioate;(+)-Diisopropyl L-tartrate, 98%, optical purity ee: 99% (GLC);Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-bis(1-methylethyl) ester;Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, bis(1-methylethyl) ester

Chemical Property of (+)-Diisopropyl L-tartrate

Chemical Property:

• Appearance/Colour: clear, colorless liquid
• Vapor Pressure: 0.00106mmHg at 25°C
• Refractive Index: 1.438 - 1.440
• Boiling Point: 268.1 °C at 760 mmHg
• PKA: 11.70±0.20(Predicted)
• Flash Point: 109.4 °C
• PSA: 93.06000
• Density: 1.188 g/cm³
• LogP: -0.38860
• Storage Temp.: Refrigerator
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 234.11033829
• Heavy Atom Count: 16
• Complexity: 222

Purity/Quality:

98% ^*data from raw suppliers

(+)-Diisopropyl L-tartrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)OC(=O)C(C(C(=O)OC(C)C)O)O
• Isomeric SMILES: CC(C)OC(=O)[C@@H]([C@H](C(=O)OC(C)C)O)O
• Uses: (+)-Diisopropyl L-Tartrate is a reagent for kinetic resolution of racemic allylic alcohols and α-furfuryl amides by enantioselective epoxidation. Both D- and L-forms are reagents for kinetic resolution of racemic allylic alcohols and α-furfuryl amides by enantioselective epoxidation.

Technology Process of (+)-Diisopropyl L-tartrate

There total 15 articles about (+)-Diisopropyl L-tartrate 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: 87.0%

diethyl (2R,3R)-tartrate (87-91-2) + isopropyl alcohol (67-63-0,8013-70-5) → L-(+)-diisopropyl tartrate (2217-15-4)

Guidance literature:

With indium; iodine; for 7h; Heating;

DOI:10.1021/jo980157y

Reference yield:

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + 2,3-dimethyl-2,3-butane diol (76-09-5) → L-(+)-diisopropyl tartrate (2217-15-4) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6)

Guidance literature:

In chloroform-d1; at 20 ℃; for 48h; Title compound not separated from byproducts.;

DOI:10.1007/s00706-007-0699-x

Reference yield:

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate (1061180-99-1) + pinanediol (18680-27-8) → L-(+)-diisopropyl tartrate (2217-15-4) + (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-phenylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole (76110-78-6)

Guidance literature:

In chloroform-d1; at 20 ℃; for 0.25h; Title compound not separated from byproducts.;

DOI:10.1007/s00706-007-0699-x

upstream raw materials:

tartaric acid

isopropyl alcohol

diethyl (2R,3R)-tartrate

(4R,5R)-diisopropyl-2-phenyl-1,3,2-dioxaborolane-4,5-dicarboxylate

Downstream raw materials:

Di(1-methylethyl)-(2R,3R)-2,3-bis<(trimethylsilyl)oxy>butandioat

(R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol

(4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol

(2R)-diisopropyl 2-hydroxybutanedioate

Refernces

Total synthesis of the L-hexoses

10.1016/S0040-4020(01)97596-9

The research focuses on the total synthesis of L-hexoses, which are enantiomerically pure polyhydroxylated natural products. The purpose of this study was to demonstrate the power of the "reagent-control" strategy in organic chemistry, which utilizes powerful asymmetric reagents and catalysts to construct any stereochemical combination, including those that are difficult to make using traditional "substrate-control" methods. The researchers employed a reiterative two-carbon extension cycle consisting of four key transformations: conversion of an aldehyde to an allylic alcohol, asymmetric epoxidation, regioselective opening of the epoxy alcohol, and oxidation to generate a bis-homologated aldehyde. Chemicals used in the process include aldehydes, allylic alcohols, L-(+)-diisopropyl tartrate, titanium tetraisopropoxide, t-butylhydroperoxide, benzenethiol, and various Wittig reagents for olefination, among others. The conclusions of the research confirmed the efficiency and generality of the reagent-control methodology in the total synthesis of all eight L-hexoses, showcasing its potential for selective construction of any one of the sixteen hexose stereoisomers.

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