Diisopropyl (S)-(-)-malate

Base Information

• Chemical Name: Diisopropyl (S)-(-)-malate
• CAS No.: 83541-68-8
• Molecular Formula: C₁₀H₁₈O₅
• Molecular Weight: 218.25
• Hs Code.: 2918199090
• European Community (EC) Number: 628-264-8
• DSSTox Substance ID: DTXSID50462659
• Nikkaji Number: J1.161.632A
• Wikidata: Q82287224
• Mol file: 83541-68-8.mol

Synonyms:(-)-Diisopropyl-L-Malate;Diisopropyl (S)-(-)-malate;83541-68-8;dipropan-2-yl (2S)-2-hydroxybutanedioate;(S)-diisopropyl malate;diisopropyl-(S)-(-)-malate;SCHEMBL1828782;DTXSID50462659;XYVHRFVONMVDGK-QMMMGPOBSA-N;Diisopropyl (S)-2-hydroxysuccinate;Diisopropyl (S)-(-)-malate, 99%;AKOS015894432;AS-59994;CS-0456078;1,4-bis(propan-2-yl) (2S)-2-hydroxybutanedioate

Chemical Property of Diisopropyl (S)-(-)-malate

Chemical Property:

• Vapor Pressure: 5.75E-05mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Boiling Point: 237 °C(lit.)
• Flash Point: >230 °F
• PSA: 89.49000
• Density: 1.055 g/mL at 25 °C(lit.)
• LogP: -1.30390
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 218.11542367
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

(-)-Diisopropyl-L-malate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)OC(=O)CC(C(=O)OC(C)C)O
• Isomeric SMILES: CC(C)OC(=O)C[C@@H](C(=O)OC(C)C)O
• Uses: Diisopropyl (S)-(?)-malate can be used as a starting material in the total synthesis of (?)-wikstromol, an α-hydroxylated lactone lignan found in Asian medicinal plants.

Technology Process of Diisopropyl (S)-(-)-malate

There total 5 articles about Diisopropyl (S)-(-)-malate 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: 70.0%

(S)-Malic acid (97-67-6,78644-42-5) + isopropyl alcohol (67-63-0,8013-70-5) → 2S-Hydroxybutan-1,4-dioic acid diisopropyl ester (83541-68-8,6947-09-7)

Guidance literature:

With thionyl chloride; Heating;

DOI:10.1002/hlca.19840670631

Reference yield:

(4S,5S)-2,2-Dioxo-2λ6-[1,3,2]dioxathiolane-4,5-dicarboxylic acid diisopropyl ester (127854-45-9,117470-88-9) → 2S-Hydroxybutan-1,4-dioic acid diisopropyl ester (83541-68-8,6947-09-7)

Guidance literature:

With sulfuric acid; sodium cyanoborohydride; Yield given. Multistep reaction; 1.) THF, 65 deg C, 2 h, 2.) ether, 25 deg C, 12 h;

DOI:10.1021/ja00230a045

Reference yield:

D-(-)-diisopropyl tartrate (62961-64-2) → 2S-Hydroxybutan-1,4-dioic acid diisopropyl ester (83541-68-8,6947-09-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) thionyl chloride, 2.) NaIO₄, RuCl₃*3H₂O / 1.) CCl₄, reflux, 30 min, 2.) CH₃CN/H₂O, room temperature, 60 min

2: 1.) NaBH₃CN, 2.) 20 percent aq. H₂SO₄ / 1.) THF, 65 deg C, 2 h, 2.) ether, 25 deg C, 12 h

With ruthenium trichloride; sodium periodate; thionyl chloride; sulfuric acid; sodium cyanoborohydride;

DOI:10.1021/ja00230a045

upstream raw materials:

(4S,5S)-2,2-Dioxo-2λ⁶-[1,3,2]dioxathiolane-4,5-dicarboxylic acid diisopropyl ester

(S)-Malic acid

isopropyl alcohol

2-iodo-propane

Downstream raw materials:

2R-[3-(4-ethoxy-phenyl)-propyl]-3S-hydroxy-succinic acid diisopropylester

(2R,3S)-2-Hydroxy-3-(3-methoxy-benzyl)-succinic acid diisopropyl ester

(2R,3S)-2-[4-(benzyloxy)-3-methoxybenzyl]-3-hydroxybutanedioic acid diisopropyl ester