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

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

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

• 6087-46-3 methyl 2,3,4-tri-O-acetyl-6-chloro-6-deoxy-α-D-glucopyranoside 
• 85716-44-5 methyl 2,3,4-tri-O-benzyl-α-d-xylo-hex-5-enopyranoside 
• 129905-38-0 methyl-6-S-phenyl-6-thio-α-D-glucopyranoside 
• 23701-87-3 methyl 6-azido-6-deoxy-α-D-glucopyranoside 
• 24809-76-5 6-Desoxy-α-D-glucopyranosyl-phosphat 
• 289901-74-2 1,2,3,4-tetra-O-benzoyl-6-deoxy-D-glucopyranose 
• 19083-14-8 uridine 5'-(6-deoxy-α-D-glucopyranosyl diphosphate) 
• 289901-76-4 ethyl 2,3,4-tri-O-benzyl-6-deoxy-1-thio-β-D-glucopyranoside 
• 289901-75-3 ethyl 2,3,4-tri-O-benzoyl-6-deoxy-1-thio-β-D-glucopyranoside 
• 120449-27-6 dibenzyl-(2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl) phosphate 
• 24988-24-7 thymidine 5'-(6-deoxy-α-D-glucopyranosyl diphosphate) 
• 85798-11-4 (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one 
• 606930-14-7 (2S,3R,4S)-2,3,4-tris-benzyloxy-5-hydroxycyclohexan-1-one 
• 129905-39-1 methyl 2,3,4-tri-O-acetyl-6-deoxy-6-phenylthio-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.

Synthesis and Structural Characteristics of all Mono- And Difluorinated 4,6-Dideoxy- d - Xylo-hexopyranoses

Protein-carbohydrate interactions are implicated in many biochemical/biological processes that are fundamental to life and to human health. Fluorinated carbohydrate analogues play an important role in the study of these interactions and find application a

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

Enolic ortho esters. VI* A new 'pyranose → cyclohexane' transformation via 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-xylo-hex-5-enopyranose

Hydrolysis of methyl 6-chloro-6-deoxy-2,3,4-tri-O-methyl-α-D-glucopyranoside (19b) and Swern oxidation of the resulting anomeric hemiacetals (20) gave 6-chloro-6-deoxy-2,3,4-tri-O-methyl-D-glucono-1,5-lactone (21), treatment of which with 1,2-bis(trimethylsilyloxy)ethane in the presence of trimethylsilyl trifluoromethanesulfonate gave 6-chloro-1,6-dideoxy-1,1-ethylenedioxy-2,3,4-tri-O-methyl-D-glucopyranose (23a). Conversion of (23a) into the corresponding 6-iodo compound (23b) and treatment of this with 1,8-diazabicyclo[5.4.0]undec-7-ene afforded the enolic ortho ester 1,6-dideoxy-1,1-ethylenedioxy-2,3,4-triO-methyl-D-xylo-hex-5-enopyranose (26). Reaction of (26) with methylmagnesium iodide, or with titanium tetrachloride, gave (1R,6S,7R,8R,9S)-7,8,9-trimethoxy-6-methyl-2,5-dioxabicyclo[4.3.1]decan-1-ol (34), or (2S,3R,4R)-5,5-ethylenedioxy-2,3,4-trimethoxycyclohexanone (28), respectively.

Synthesis of new aminocyclitols as potent enzymatic inhibitors

The syntheses of new pseudo-saccharides having an allylic amino moiety or an aziridine group are reported starting from methyl-α-D-glucopyranoside. To enhance the hydrophilic/lipophilic balance, pseudo-saccharides 9 and 10 were linked with a glycosyl deri