(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester
• CAS No.: 37031-30-4
• Molecular Formula: C₉H₁₄O₆
• Molecular Weight: 218.207
• Hs Code.: 29329900
• DSSTox Substance ID: DTXSID001169504
• Nikkaji Number: J635.634F
• Mol file: 37031-30-4.mol

Synonyms:37031-30-4;(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester;(4S,5S)-Dimethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate;Dimethyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate;(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate;(+)-Dimethyl-2,3-o-isopropylidene-d-tartrate;Dimethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate #;SCHEMBL10266772;1,3-Dioxolane-4,5-dicarboxylic acid, 2,2-dimethyl-, dimethyl ester, (4S,5S)-;DTXSID001169504;MFCD00040504;AKOS030632709;CS-W014798;A6373;I0474;(+)-Dimethyl-2,3-O-isopropylidine-D-tartrate;D91161;Dimethyl (+)-2,3-O-Isopropylidene-D-tartrate;J-640441;J-800409;(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate, 98%;2-O,3-O-Isopropylidene-D-tartaric acid dimethyl ester;(+)-2,3-O-Isopropylidene-D-tartaric Acid Dimethyl Ester;(4S,5S)-Dimethyl2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate;4,5-dimethyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Chemical Property of (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquild
• Vapor Pressure: 0.00693mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Boiling Point: 270.222 °C at 760 mmHg
• Flash Point: 135 °C
• PSA: 71.06000
• Density: 1.183 g/cm³
• LogP: -0.14750
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Methanol
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 218.07903816
• Heavy Atom Count: 15
• Complexity: 246

Purity/Quality:

97% ^*data from raw suppliers

2,3-O-Isopropylidene-D-tartaricAcid,DimethylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(C(O1)C(=O)OC)C(=O)OC)C
• Isomeric SMILES: CC1(O[C@@H]([C@H](O1)C(=O)OC)C(=O)OC)C
• Uses: (+)-Dimethyl 2,3-O-isopropylidene-D-tartrate can be used as a starting material for the synthesis of: Deuterated 1-deoxy-D-xylose. C-terminal peptide -oxo-aldehydes using Fmoc solid-phase peptide synthesis methodology (SPPS). Bis-Weinreb amide, a key intermediate for the preparation of myo-inositol analog via ring-closing metathesis.

Technology Process of (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester

There total 12 articles about (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester 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%

D-tartaric acid (147-71-7,138508-61-9) + 2,2-dimethoxy-propane (77-76-9) → (+)-dimethyl-2,3-O-isopropylidene-D-tartrate (37031-29-1,6134-82-3,6135-80-4,90613-41-5,116499-08-2,37031-30-4)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; cyclohexane; at 52 - 54 ℃;

DOI:10.1016/S0040-4039(01)01338-7

Reference yield: 90.0%

(4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (73346-73-3) + phenylmagnesium bromide → (S,S)-taddol (93222-42-5,93379-48-7,93379-49-8,118139-82-5,126639-52-9,37031-30-4)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)80147-1

Reference yield: 89.3%

Dimethyl D-tartrate (13171-64-7) + 2,2-dimethoxy-propane (77-76-9) → (+)-dimethyl-2,3-O-isopropylidene-D-tartrate (37031-29-1,6134-82-3,6135-80-4,90613-41-5,116499-08-2,37031-30-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 6h; Reflux;

DOI:10.1016/j.tetlet.2013.09.120

upstream raw materials:

methanol

D-tartaric acid

2,2-dimethoxy-propane

Dimethyl D-tartrate

Downstream raw materials:

(S,S)-(-)-N,N,N',N'-tetramethyl-2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxamide

(2S,3R)-5-(bis-benzyloxyphosphoryloxymethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid

dibenzyl (2S,3R)-5-hydroxycarbamoyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl phosphate

dibenzyl (2S,3R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl phosphate