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85026-59-1

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85026-59-1 Usage

General Description

The chemical (1R,2S,3R,5R)-3-aMino-5-(hydroxyMethyl)cyclopentane-1,2-diol is a compound with a cyclopentane ring structure and two hydroxyl groups. It also contains an amino group and a hydroxymethyl group. (1R,2S,3R,5R)-3-aMino-5-(hydroxyMethyl)cyclopentane-1,2-diol is a stereoisomer, with the 1R,2S,3R,5R configuration. It is commonly used in pharmaceuticals and biochemistry as a chiral building block for the synthesis of more complex compounds. The presence of the amino and hydroxyl groups makes it potentially useful in drug development and as a starting material in organic synthesis.

Check Digit Verification of cas no

The CAS Registry Mumber 85026-59-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,5,0,2 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 85026-59:
(7*8)+(6*5)+(5*0)+(4*2)+(3*6)+(2*5)+(1*9)=131
131 % 10 = 1
So 85026-59-1 is a valid CAS Registry Number.

85026-59-1SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name (-)-(amino-cis-4-dihydroxy-trans-2,3-hydroxymethyl)-1 cyclopentane

1.2 Other means of identification

Product number -
Other names (4a-carba-β-D-ribofuranosyl)amine

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:85026-59-1 SDS

85026-59-1Relevant articles and documents

Synthesis of 4a-Carba-d-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases

Zaji?ková, Mária,Monco?, Ján,?esták, Sergej,Kóňa, Juraj,Koó?, Miroslav,Bella, Maro?

, p. 1114 - 1124 (2019/01/24)

A synthetic approach to 4a-carba-d-lyxofuranose derivatives starting from d-lyxose is described. The protected 4a-carba-β-d-lyxofuranose was employed as the key intermediate for the synthesis of 4a-carba-d-lyxofuranose derivatives including novel 1-amino-1-deoxy-4a-carba-d-lyxofuranoses. Synthesized 4a-carba-d-lyxofuranoses were evaluated as inhibitors of GH38 α-mannosidases, namely, the Golgi (GMIIb) and lysosomal (LManII) α-mannosidases from Drosophila melanogaster and commercial Jack bean α-mannosidase (JBMan) from Canavalia ensiformis. The biochemical evaluation revealed that only 1-amino-1-deoxy-4a-carba-β-d-lyxofuranose exhibited reasonable inhibitory activity against GMIIb (IC50 = 200 μm). In addition, the results of biological evaluation were discussed by means of molecular modelling.

Synthesis of carba-NAD and the structures of its ternary complexes with SIRT3 and SIRT5

Szczepankiewicz, Bruce G.,Dai, Han,Koppetsch, Karsten J.,Qian, Dongming,Jiang, Fan,Mao, Cheney,Perni, Robert B.

, p. 7319 - 7329 (2012/11/13)

Carba-NAD is a synthetic compound identical to NAD except for one substitution, where an oxygen atom adjacent to the anomeric linkage bearing nicotinamide is replaced with a methylene group. Because it is inert in nicotinamide displacement reactions, carba-NAD is an unreactive substrate analogue for NAD-consuming enzymes. SIRT3 and SIRT5 are NAD-consuming enzymes that are potential therapeutic targets for the treatment of metabolic diseases and cancers. We report an improved carba-NAD synthesis, including a pyrophosphate coupling method that proceeds in approximately 60% yield. We also disclose the X-ray crystal structures of the ternary complexes of SIRT3 and SIRT5 bound to a peptide substrate and carba-NAD. These X-ray crystal structures provide critical snapshots of the mechanism by which human sirtuins function as protein deacylation catalysts.

Variable strategy toward carbasugars and relatives. 4. Viable access to (4a-carbapentofuranosyl)amines, (5a-carbahexopyranosyl)amines, and amino acids thereof

Rassu, Gloria,Auzzas, Luciana,Pinna, Luigi,Zambrano, Vincenzo,Zanardi, Franca,Battistini, Lucia,Marzocchi, Lucia,Acquotti, Domenico,Casiraghi, Giovanni

, p. 5338 - 5342 (2007/10/03)

A chiral, divergent synthesis of two carbafuranosylamines, 1 and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)-oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.

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