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(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.

37031-30-4

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  • (+)-dimethyl-2,3-O-isopropylidene-D-tartrate, dimethyl (4S,5S)-(-)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate, (4S,5S)-dimethyl-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate, dimethyl (4S,5S)-2,2-dim

    Cas No: 37031-30-4

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37031-30-4 Usage

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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.

Check Digit Verification of cas no

The CAS Registry Mumber 37031-30-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,7,0,3 and 1 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 37031-30:
(7*3)+(6*7)+(5*0)+(4*3)+(3*1)+(2*3)+(1*0)=84
84 % 10 = 4
So 37031-30-4 is a valid CAS Registry Number.
InChI:InChI=1/C9H14O6/c1-9(2)14-5(7(10)12-3)6(15-9)8(11)13-4/h5-6H,1-4H3

37031-30-4 Well-known Company Product Price

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  • TCI America

  • (I0474)  Dimethyl (+)-2,3-O-Isopropylidene-D-tartrate  >95.0%(GC)

  • 37031-30-4

  • 5g

  • 720.00CNY

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  • Aldrich

  • (384313)  (+)-Dimethyl2,3-O-isopropylidene-D-tartrate  98%

  • 37031-30-4

  • 384313-5G

  • 966.42CNY

  • Detail

37031-30-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (4S,5S)-2,2-DIMETHYL-1,3-DIOXOLANE-4,5-DICARBOXYLIC ACID DIMETHYL ESTER

1.2 Other means of identification

Product number -
Other names (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic Acid Dimethyl Ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:37031-30-4 SDS

37031-30-4Downstream Products

37031-30-4Relevant articles and documents

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

Luan, Yu-Xin,Peng, Qian,Ye, Mengchun,Zhang, Tao,Zheng, Su-Juan

supporting information, p. 7439 - 7443 (2020/03/24)

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

Miyazawa, Yuki,Sugimoto, Makoto,Tanaka-Oda, Ayumi,Makabe, Hidefumi

, (2019/08/16)

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.

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

Zhang, Zhao-Fei,Yang, Xiao-Chao,Lu, Hui-Jie,Wang, Min-Can

, p. 785 - 793 (2018/02/21)

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

Daugey,De Rycke,Brotin,Buffeteau

supporting information, p. 342 - 350 (2018/01/15)

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.

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

Davis, Robert W.,Allweil, Alexander,Tian, Jianhua,Brash, Alan R.,Sulikowski, Gary A.

supporting information, p. 4571 - 4573 (2018/11/23)

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.

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

Liu, Qi-Sheng,Wang, De-Yin,Yang, Zhi-Jun,Luan, Yu-Xin,Yang, Jin-Fei,Li, Jiang-Fei,Pu, You-Ge,Ye, Mengchun

supporting information, p. 18150 - 18153 (2017/12/27)

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

Raghavan, Sadagopan,Nyalata, Satyanarayana

supporting information, p. 10698 - 10706 (2016/11/29)

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.

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

Allmendinger, Simon,Kinuta, Hirotaka,Breit, Bernhard

supporting information, p. 41 - 45 (2015/03/03)

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.

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

Gao, Xing,Han, Jianwei,Wang, Limin

supporting information, p. 4596 - 4599 (2015/09/28)

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.

Versicolactones A and B: Total synthesis and structure revision

Wang, Liping,Zhu, Weiming

supporting information, p. 6729 - 6731 (2013/11/19)

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.

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