37031-30-4

Basic information

• Product Name: (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER
• Synonyms: Dimethyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate, (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester;(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate,97%;4S,5S-diethyl 2,2-diMethyl-1,3-dioxolane-4,5-dicarboxylate;Dimethyl (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylate (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic Acid Dimethyl Ester (+)-2,3-O-Isopropylidene-D-tartaric Acid Dimethyl Ester;2,2-Dimethyl-(4S-trans)-1,3-Dioxolane-4,5-dicarboxylic acid dimethyl ester;(+)-DiMethyl 2,3-O-isopropylidene-D-tartarate , GC 97%;(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate 98%;(4S,5S)- 2,2-dimethyl-1,3-Dioxolane-4,5-dicarboxylic acid 4,5-dimethyl ester
• CAS NO: 37031-30-4
• Molecular Formula: C₉H₁₄O₆
• Molecular Weight: 218.2
• Product Categories: Dioxolanes;Esters (Chiral);Synthetic Organic Chemistry;Amino Acids & Derivatives;chiral;Amino Acids 13C, 2H, 15N;Chiral Building Blocks;Dioxanes & Dioxolanes
• Mol File: 37031-30-4.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 80-82 °C0.1 mm Hg(lit.)
• Flash Point: 275 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.19 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00693mmHg at 25°C
• Refractive Index: n20/D 1.439(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• BRN: 3548490
• CAS DataBase Reference: (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER(37031-30-4)
• EPA Substance Registry System: (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER(37031-30-4)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 37031-30-4(Hazardous Substances Data)

Usage

Description

(4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER is a chiral compound with a unique structure, characterized by its 4S,5S configuration and dioxolane ring. It is a colorless to light yellow liquid, which is commonly used as a starting material in the synthesis of various organic compounds.

Uses

Used in Pharmaceutical Industry:
(4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER is used as a starting material for the synthesis of deuterated 1-deoxy-D-xylose, which is an essential component in the development of pharmaceuticals targeting various diseases.
Used in Peptide Synthesis:
In the field of peptide synthesis, (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER is used as a key intermediate for the preparation of C-terminal peptide-oxo-aldehydes using Fmoc solid-phase peptide synthesis methodology (SPPS). This application is crucial for the development of novel peptide-based therapeutics.
Used in Organic Synthesis:
(4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER serves as a chiral reagent in organic synthesis, particularly for the preparation of myo-inositol analogs via ring-closing metathesis. This process is vital for the synthesis of complex organic molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Used in Chemical Research:
As a chiral compound with unique structural features, (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER is also used in chemical research to study the properties and reactivity of chiral molecules, which can lead to the discovery of new synthetic routes and applications in various fields.

InChI:InChI=1/C9H14O6/c1-9(2)14-5(7(10)12-3)6(15-9)8(11)13-4/h5-6H,1-4H3

Upstream product

• 67-56-1 methanol 
• 147-71-7 D-tartaric acid 
• 77-76-9 2,2-dimethoxy-propane 
• 13171-64-7 Dimethyl D-tartrate 
• 17081-21-9 1,3-dimethoxy propane 
• 67-64-1 acetone 
• 73346-73-3 (4S,5S)-diethyl 2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 108-86-1 bromobenzene 
• 37031-29-1 (+)-dimethyl-2,3-O-isopropylidene-D-tartrate 

Downstream Products

• 121463-31-8 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1-methyl-1H-pyridin-2-one 
• 121463-33-0 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,5-dimethyl-1H-pyridin-2-one 
• 121463-32-9 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,6-dimethyl-1H-pyridin-2-one 
• 121471-25-8 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,4-dimethyl-1H-pyridin-2-one 
• 121463-34-1 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4-methoxy-1-methyl-1H-pyridin-2-one 
• 117859-43-5 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 7a-methyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione 
• 117780-11-7 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1,4,5,6,7,7a-hexahydro-inden-2-one 
• 117859-41-3 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 117780-13-9 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4a-ethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 121463-35-2 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 4-ethoxy-1-methyl-1H-pyridin-2-one 
• 1445-91-6 (S)-1-phenylethanol 
• 1517-69-7 (R)-1-phenylethanol 
• 73346-74-4 (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol 
• 182966-70-7 (4S,5S)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 

Relevant articles and documents

Chiral Aluminum Complex Controls Enantioselective Nickel-Catalyzed Synthesis of Indenes: C?CN Bond Activation

A chiral aluminum complex controlled, enantioselective nickel-catalyzed domino reaction of aryl nitriles and alkynes proceeding by C?CN bond activation was developed. The reaction provides various indenes, bearing chiral all-carbon quaternary centers, under mild reaction conditions in yields of 32 to 91 percent and ee values within the 73–98 percent range. The reaction mechanism and aspects of stereocontrol were investigated by DFT calculations.

Chiroptical properties of 2,2’-bioxirane

The two enantiomers of 2,2′-bioxirane were synthesized, and their chiroptical properties were thoroughly investigated in various solvents by polarimetry, vibrational circular dichroism (VCD), and Raman optical activity (ROA). Density functional theory (DFT) calculations at the B3LYP/aug-cc-pVTZ level revealed the presence of three conformers (G+, G?, and cis) with Gibbs populations of 51, 44, and 5% for the isolated molecule, respectively. The population ratios of the two main conformers were modified for solvents exhibiting higher dielectric constants (G? form decreases whereas G+ form increases). The behavior of the specific optical rotation values with the different solvents was correctly reproduced by time-dependent DFT calculations using the polarizable continuum model (PCM), except for the benzene for which explicit solvent model should be necessary. Finally, VCD and ROA spectra were perfectly reproduced by the DFT/PCM calculations for the Boltzmann-averaged G+ and G? conformers.

Enantioselective Direct Synthesis of syn- and anti-α,β-Dihydroxy γ-Keto Esters Using a Dinuclear Zinc–AzePhenol Complex

A one-step enantioselective direct synthesis of both syn- and anti-α,β-dihydroxy γ-keto esters using a dinuclear zinc–AzePhenol complex is presented. This asymmetric α-hydroxyacetate aldol reaction proceeds in moderate to good yield and with excellent ena