99409-32-2

Basic information

• Product Name: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside
• Synonyms: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside;Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-thioglucopyranoside;Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-glucopyranoside;Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside;Ethyl 3,4,6-tri-O-Acetyl-2-deoxy-2-phthalimido-β-D-thioglucopyranoside, 98%
• CAS NO: 99409-32-2
• Molecular Formula: C₂₂H₂₅NO₉S
• Molecular Weight: 479.5002
• Mol File: 99409-32-2.mol
• Article Data: 32

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside(99409-32-2)
• EPA Substance Registry System: Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside(99409-32-2)

Safety Data

• Hazardous Substances Data: 99409-32-2(Hazardous Substances Data)

Usage

Description

Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside is a complex organic compound that serves as a key intermediate in the synthesis of various biologically active molecules. It is characterized by its unique structure, which includes an ethyl group, three acetyl groups, a deoxy sugar moiety, and a phthalimido group. Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside plays a crucial role in the development of pharmaceuticals and other applications.

Uses

Used in Pharmaceutical Industry:
Ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-b-D-thioglucopyranoside is used as a reactant in the synthesis of Me 2-amino-2-deoxy-a-D-glucopyranoside 6-phosphate and Me 2-amino-2-deoxy-b-D-glucopyranoside 6-phosphate. These synthesized compounds act as cell wall inhibitors targeting the GlmM and GlmU enzymes in Mycobacterium tuberculosis, which are responsible for the biosynthesis of a key component of bacterial cell walls. By inhibiting these enzymes, the compound can potentially contribute to the development of new treatments for tuberculosis.

Upstream product

• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 75-08-1 ethanethiol 
• 72858-55-0 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose 
• 31505-42-7 2-(2-carboxybenzamido)-2-deoxy-D-glucopyranose 
• 90-76-6 2-deoxy-2-amino glucose 
• 85-44-9 phthalic anhydride 
• 138906-41-9 4-methoxylphenzyl 2-deoxy-2-phthalimido-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 17460-45-6 tetra-acetyl glucosamine 
• 31505-46-1 tetra-O-acetyl-2-(2-carboxy-benzoylamino)-2-deoxy-β-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 4710-95-6 D-mannosamine hydrochloride 
• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 63000-70-4 C₂₀H₂₀INO₉ 

Downstream Products

• 118579-75-2 methyl 2-O-benzyl-4,6-O-benzylidene-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 104707-08-6 1,2,3,4-tetra-O-benzoyl-6-O-(3,4-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-glucopyranose 
• 140686-53-9 p-nitrophenyl 2-azido-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-β-D-mannopyranoside 
• 130539-43-4 ethyl 2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 1334525-90-4 ethyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-trifluoromethanesulfonyl-1-thio-β-D-glucopyranoside 
• 1334525-91-5 ethyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-allopyranoside 
• 1334525-92-6 ethyl 2-azido-4,6-O-benzylidene-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside 
• 1334525-93-7 ethyl 2-azido-4,6-di-O-benzyl-2,3-dideoxy-3-fluoro-1-thio-β-D-glucopyranoside 
• 1371585-26-0 methyl 2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 1371585-27-1 methyl 2-amino-2-deoxy-β-D-glucopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1371585-28-2 methyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1371585-29-3 methyl β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 136198-40-8 methyl-N,N'-diacetyl-β-chitobioside 
• 97242-79-0 methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 

Relevant articles and documents

ANTIMICROBIAL VACCINE COMPOSITIONS

This invention is directed to antimicrobial vaccine compounds and compositions comprising oligosaccharide β-(1→6)- glucosamine groups having from 3 to 12 glucosamine units linked through a linker group to tetanus toxoid wherein the toxoid is primarily in

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Disclosed are antimicrobial vaccines comprising oligosaccharide β-(1→6)-glucosamine groups.

Chemoenzymatic Synthesis of Glycoconjugates Mediated by Regioselective Enzymatic Hydrolysis of Acetylated 2-Amino Pyranose Derivatives

Highly regioselective deprotection of a series of 2-amino pyranose building blocks was achieved by enzymatic hydrolysis. These monodeprotected intermediates were successfully used in the synthesis of a variety of glycoconjugate derivatives with a core of glucosamine or galactosamine, including neo-glycoproteins and glycosphingolipids. The hydrolysis catalyzed by acetylxylan esterase from Bacillus pumilus (AXE) is suitable for the synthesis of neo-glycoproteins with an N-acetyl glucosamine core. The hydrolysis catalyzed by Candida rugosa lipase (CRL) was successfully applied in the preparation of new sialylated glycolipids starting from glucosamine building blocks protected as phthalimide. This chemoenzymatic approach can be used for the preparation of new glycoconjugate products with anticancer activity.