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930-46-1

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930-46-1 Usage

Description

(1R)-TRANS-1,2-CYCLOPENTANEDIOL is a chiral organic compound with the molecular formula C5H10O2. It is characterized by its unique trans-1,2-cyclopentanediol structure and the R-configuration at the first carbon atom. (1R)-TRANS-1,2-CYCLOPENTANEDIOL is known for its potential use as a chiral auxiliary in various chemical reactions and as a building block for the synthesis of chiral phosphine ligands.

Uses

Used in Pharmaceutical Industry:
(1R)-TRANS-1,2-CYCLOPENTANEDIOL is used as a chiral auxiliary for the synthesis of chiral compounds, which are essential in the development of pharmaceutical drugs. The chiral nature of this compound allows for the creation of enantiomerically pure products, which is crucial for the effectiveness and safety of many medications.
Used in Chemical Synthesis:
(1R)-TRANS-1,2-CYCLOPENTANEDIOL serves as a building block for the synthesis of chiral phosphine ligands. These ligands are vital components in various catalytic reactions, particularly in asymmetric catalysis, where they help to achieve high levels of enantioselectivity and improve the efficiency of chemical processes.
Used in Research and Development:
(1R)-TRANS-1,2-CYCLOPENTANEDIOL is also utilized in research and development settings, where it can be employed to study the effects of chirality on chemical reactions and to develop new methods for the synthesis of enantiomerically pure compounds. This research can lead to advancements in various fields, including pharmaceuticals, materials science, and agrochemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 930-46-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 9,3 and 0 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 930-46:
(5*9)+(4*3)+(3*0)+(2*4)+(1*6)=71
71 % 10 = 1
So 930-46-1 is a valid CAS Registry Number.
InChI:InChI=1/C5H10O2/c6-4-2-1-3-5(4)7/h4-7H,1-3H2/t4-,5-/m1/s1

930-46-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 14, 2017

Revision Date: Aug 14, 2017

1.Identification

1.1 GHS Product identifier

Product name (1R,2R)-1,2-Cyclopentanediol

1.2 Other means of identification

Product number -
Other names (1r,2r)-diaminocyclohexane

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:930-46-1 SDS

930-46-1Relevant articles and documents

One-Pot Enzymatic Synthesis of Cyclic Vicinal Diols from Aliphatic Dialdehydes via Intramolecular C?C Bond Formation and Carbonyl Reduction Using Pyruvate Decarboxylases and Alcohol Dehydrogenases

Zhang, Yan,Yao, Peiyuan,Cui, Yunfeng,Wu, Qiaqing,Zhu, Dunming

supporting information, p. 4191 - 4196 (2018/09/25)

An enzymatic cascade reaction was developed for one-pot enantioselective conversion of aliphatic dialdehydes to chiral vicinal diols using pyruvate decarboxylases (PDCs) and alcohol dehydrogenases (ADHs). The PDCs showed promiscuity in catalysing the cyclization of aliphatic dialdehydes through intramolecular stereoselective carbon-carbon bond formation. Consequently, 1,2-cyclopentanediols in three different stereoisomeric forms and 1,2-cyclohexanediols in two different stereoisomeric forms could be prepared with high conversion and stereoisomeric ratio from the respective initial substrates, glutaraldehyde and adipaldehyde. These cascade reactions represent a promising approach to the biocatalytic synthesis of important chiral vicinal diols. (Figure presented.).

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

Fujii, Kazuki,Mitsudo, Koichi,Mandai, Hiroki,Suga, Seiji

supporting information, p. 2778 - 2788 (2017/08/23)

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

Comparing Different Strategies in Directed Evolution of Enzyme Stereoselectivity: Single- versus Double-Code Saturation Mutagenesis

Sun, Zhoutong,Lonsdale, Richard,Li, Guangyue,Reetz, Manfred T.

, p. 1865 - 1872 (2016/11/06)

Saturation mutagenesis at sites lining the binding pockets of enzymes constitutes a viable protein engineering technique for enhancing or inverting stereoselectivity. Statistical analysis shows that oversampling in the screening step (the bottleneck) increases astronomically as the number of residues in the randomization site increases, which is the reason why reduced amino acid alphabets have been employed, in addition to splitting large sites into smaller ones. Limonene epoxide hydrolase (LEH) has previously served as the experimental platform in these methodological efforts, enabling comparisons between single-code saturation mutagenesis (SCSM) and triple-code saturation mutagenesis (TCSM); these employ either only one or three amino acids, respectively, as building blocks. In this study the comparative platform is extended by exploring the efficacy of double-code saturation mutagenesis (DCSM), in which the reduced amino acid alphabet consists of two members, chosen according to the principles of rational design on the basis of structural information. The hydrolytic desymmetrization of cyclohexene oxide is used as the model reaction, with formation of either (R,R)- or (S,S)-cyclohexane-1,2-diol. DCSM proves to be clearly superior to the likewise tested SCSM, affording both R,R- and S,S-selective mutants. These variants are also good catalysts in reactions of further substrates. Docking computations reveal the basis of enantioselectivity.

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