4144-87-0

Basic information

• Product Name: METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
• Synonyms: METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE;METHYL-6-CHLORO-6-ALPHA-D-GLUCOPYRANOSIDE;Methyl 6-chloro-6-deoxy-a-D-glucopyranoside;a-D-Glucopyranoside,Methyl 6-chloro-6-deoxy-
• CAS NO: 4144-87-0
• Molecular Formula: C₇H₁₃ClO₅
• Molecular Weight: 212.63
• Mol File: 4144-87-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 370.415 °C at 760 mmHg
• Flash Point: 177.821 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 5.37E-07mmHg at 25°C
• Refractive Index: 1.532
• Solubility: Ethanol, Methanol, Water
• CAS DataBase Reference: METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(4144-87-0)
• EPA Substance Registry System: METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE(4144-87-0)

Safety Data

• Hazardous Substances Data: 4144-87-0(Hazardous Substances Data)

Usage

Description

METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE is a chemical compound that serves as an intermediate in the synthesis of various pharmaceutical products. It is a derivative of glucose, with a chlorine atom replacing a hydroxyl group at the 6-position, and a methyl group attached to the anomeric carbon. This modification of the glucose structure allows for the development of new compounds with potential therapeutic applications.

Uses

Used in Pharmaceutical Industry:
METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE is used as an intermediate in the synthesis of 6-Chloro-6-deoxy-α-D-glucopyranose (C367760), which is a reactant used to produce carbohydrate-based antidiabetic drugs. METHYL 6-CHLORO-6-DEOXY-ALPHA-D-GLUCOPYRANOSIDE plays a crucial role in the development of new medications for the treatment of diabetes, potentially offering improved management of blood sugar levels and overall health outcomes for patients with this condition.

InChI:InChI=1/C7H13ClO5/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-7,9-11H,2H2,1H3

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 

Downstream Products

• 129905-40-4 6-S-phenyl-6-thio-α,β-D-glucose 
• 129905-41-5 6-S-phenyl-6-thio-D-glucitol 
• 129905-39-1 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylthio-α-D-glucopyranoside 
• 606930-14-7 (2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 24988-24-7 thymidine 5'-(6-deoxy-α-D-glucopyranosyl diphosphate) 
• 120449-27-6 dibenzyl-(2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) phosphate 
• 289901-75-3 ethyl 2,3,4-tri-O-benzoyl-6-deoxy-1-thio-β-D-glucopyranoside 
• 289901-76-4 ethyl 2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 
• 19083-14-8 uridine 5'-(6-deoxy-α-D-glucopyranosyl diphosphate) 
• 289901-74-2 1,2,3,4-tetra-O-benzoyl-6-deoxy-D-glucopyranose 
• 24809-76-5 6-Desoxy-α-D-glucopyranosyl-phosphat 
• 23701-87-3 methyl 6-azido-6-deoxy-α-D-glucopyranoside 
• 129905-38-0 methyl-6-S-phenyl-6-thio-α-D-glucopyranoside 

Relevant articles and documents

First homology model of Plasmodium falciparum glucose-6-phosphate dehydrogenase: Discovery of selective substrate analog-based inhibitors as novel antimalarial agents

In Plasmodium falciparum the bifunctional enzyme glucose-6-phosphate dehydrogenase?6-phosphogluconolactonase (PfG6PD?6PGL) is involved in the catalysis of the first reaction of the pentose phosphate pathway. Since this enzyme has a key role in parasite development, its unique structure represents a potential target for the discovery of antimalarial drugs. Here we describe the first 3D structural model of the G6PD domain of PfG6PD?6PGL. Compared to the human enzyme (hG6PD), the 3D model has enabled the identification of a key difference in the substrate-binding site, which involves the replacement of Arg365 in hG6PD by Asp750 in PfG6PD. In a prospective validation of the model, this critical change has been exploited to rationally design a novel family of substrate analog-based inhibitors that can display the necessary selectivity towards PfG6PD. A series of glucose derivatives featuring an α-methoxy group at the anomeric position and different side chains at position 6 bearing distinct basic functionalities has been synthesized, and their PfG6PD and hG6PD inhibitory activities and their toxicity against parasite and mammalian cells have been assessed. Several compounds displayed micromolar affinity (Ki up to 23 μM), favorable selectivity (up to > 26-fold), and low cytotoxicity. Phenotypic assays with P. falciparum cultures revealed high micromolar IC50 values, likely as a result of poor internalization of the compounds in the parasite cell. Overall, these results endorse confidence to the 3D model of PfG6PD, paving the way for the use of target-based drug design approaches in antimalarial drug discovery studies around this promising target.

Application of focused microwaves to the scale-up of solvent-free organic reactions

A series of typical solvent-free reactions have been safely and beneficially scaled-up to several hundred grams in a larger batch reactor (Synthewave 1000) with yields equivalent to those obtained under similar conditions (temperature, reaction time) in laboratory-scale experiments (Synthewave 402). They concern potassium acetate alkylation, regioselective phenacylation of 1,2,4-triazole, deethylation of 2-ethoxy-anisole, and typical examples in carbohydrate chemistry (peracetylation, glycosylation, saponification, halogenation, and epoxidation of D-glucopyranosides).

Halogenation of carbohydrates by triphenylphosphine complex reagents in highly concentrated solution under microwave activation or conventional heating

Halogenation of carbohydrates with triphenylphosphine and carbon tetrachloride, hexachloroethane or 1,2-dibromotetrachloroethane was shown to be very efficient in highly concentrated solutions of nonpolar solvents such as toluene or 1,2-dichloroethane, wi