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

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

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

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

Downstream Products

• 182966-70-7 (4S,5S)-2,2-Dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 
• 111828-49-0 (S,S)-(-)-N,N,N',N'-tetramethyl-2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxamide 
• 726189-05-5 (4S,5S)-N,N,N',N'-tetramethyl-3,4-isopropylidenedioxy-1,4-butanediamine 
• 78469-77-9 1-O-benzyl-2,3-O-isopropylidene-D-threitol 
• 91526-97-5 (4S,5R)-5-benzyloxymethyl-4-bromomethyl-2,2-dimethyl-1,3-dioxolane 
• 91526-99-7 1-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propane-2-one 
• 91526-98-6 benzyl (4R,5R)-2,2-dimethyl-5-(2-methyl-1,3-dithian-2-ylmethyl)-1,3-dioxolan-4-ylmethyl ether 
• 109715-57-3 (R,R)-4-benzyloxymethyl-2,2,5-trimethyl-1,3-dioxolane 
• 137365-16-3 (4S,5S)-2,2-dimethyl-trans-4,5-bis(di(2-naphthyl)hydroxymethyl)-1,3-dioxolane 
• 93222-42-5 (S,S)-taddol 
• 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 
• 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 
• 1598430-66-0 C₅₅H₄₆O₆P₂ 
• 299917-90-1 (3aR,8aR)-6-chloro-2,2-dimethyl-4,4,8,8-tetraphenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 

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.

Synthesis of (+)-goniopypyrone and (+)-goniotriol using Pd-catalyzed carbonylation

Syntheses of (+)-goniopypyrone and (+)-goniotriol isolated from Goniothalamus giganteus were achieved. The key steps involve Pd-catalyzed carbonylation for lactone ring formation and diastereoselective reduction of ynone using the (R)-CBS catalyst and borane dimethyl sulfide complex.

Stereocontrolled synthesis of four isomeric linoleate triols of relevance to skin barrier formation and function

Linoleate triol esters are intermediates along the pathway of formation of the mammalian skin permeability barrier. In connection with the study of their involvement in barrier formation we required access to isomerically pure and defined samples of four linoleate triol esters. A common synthetic strategy was developed starting from isomeric alkynols derived from D-tartaric acid and 2-deoxy-D-ribose.

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

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.

Ni-Al Bimetallic Catalyzed Enantioselective Cycloaddition of Cyclopropyl Carboxamide with Alkyne

A Ni-Al bimetallic catalyzed enantioselective cycloaddition reaction of cyclopropyl carboxamides with alkynes has been developed. A series of cyclopentenyl carboxamides were obtained in up to 99% yield and 94% ee. The bifunctional-ligand-enabled bimetallic catalysis proved to be an efficient strategy for the C-C bond cleavage of unreactive cyclopropanes.

Convergent Synthesis of the Dihydropyran Core Containing the C1-C15 Subunit of Sorangicin A Employing Gold(I)-Catalyzed Cyclization of an Allenic Alcohol

A convergent route to the C1-C15 subunit of sorangicin A is disclosed. The key steps include carbon-carbon bond formation using an α-chloro sulfide, regioselective hydrozirconation of an internal alkyne for the preparation of a trisubstituted iodoalkene, allene formation using the Myers-Movassaghi protocol, stereoselective reduction of allylic and propargylic ketones using Noyori's catalyst, and gold(I)-catalyzed cyclization of a β-hydroxy allene to construct the dihydropyran ring.

Design of Highly Stable Iminophosphoranes as Recyclable Organocatalysts: Application to Asymmetric Chlorinations of Oxindoles

A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.

Easily accessible TADDOL-derived bisphosphonite ligands: Synthesis and application in the asymmetric hydroformylation of vinylarenes

The synthesis of chiral bidentate bisphosphonite ligands based on the TADDOL motif from readily available starting materials has been developed. Taking advantage of the modular nature of the building blocks, a diverse ligand library has been prepared. Their catalytic potential has been evaluated in the asymmetric hydroformylation of styrene and derivatives. These catalysts showed high activity and provided the aldehydes in high enantiomeric purity.

Versicolactones A and B: Total synthesis and structure revision

To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The 1H and 13C NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta- 2,4-dien-4-lactone, respectively.