117781-06-3

Basic information

• Product Name: (S)-1-((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)-ETHANE-1,2-DIOL
• Synonyms: (S)-1-((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)-ETHANE-1,2-DIOL
• CAS NO: 117781-06-3
• Molecular Formula: C₁₆H₂₃NO₄
• Molecular Weight: 293.35812
• Mol File: 117781-06-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-1-((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)-ETHANE-1,2-DIOL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)-ETHANE-1,2-DIOL(117781-06-3)
• EPA Substance Registry System: (S)-1-((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)-ETHANE-1,2-DIOL(117781-06-3)

Safety Data

• Hazardous Substances Data: 117781-06-3(Hazardous Substances Data)

Usage

General Description

The chemical (S)-1-((3AR,4R,6AS)-5-BENZYL-2,2-DIMETHYL-TETRAHYDRO-[1,3]DIOXOLO[4,5-C]PYRROL-4-YL)-ETHANE-1,2-DIOL is a complex organic compound with a molecular structure containing a dioxolopyrrol moiety and an ethane-1,2-diol moiety. It is a chiral molecule with a stereocenter, and its (S) configuration indicates its stereochemistry. The compound also contains a benzyl group and two methyl groups, contributing to its overall structure and properties. The precise biological or chemical significance of this compound would depend on its specific context, such as its role in a particular reaction, its interactions with other molecules, or its potential pharmacological activity.

Upstream product

• 117770-02-2 (3aS,4S,6aR)-5-benzyl-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyltetrahydro-4H-[1,3]dioxolo[4,5-c]pyrrole 
• 14131-84-1 2,3:5,6-di-O-isopropylidene-α-D-mannofuranose 
• 7115-24-4 (R)-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]((4R,5R)-2,2-dimethyl-5-{[(methylsulfonyl)oxy]methyl}-1,3-dioxolan-4-yl)methyl methanesulfonate 
• 3969-61-7 2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol 
• 7757-38-2 2,3,5,6-di-O-isopropylidene-D-mannofuranose 

Downstream Products

• 117770-04-4 N-benzyl-1,4-dideoxy-1,4-imino-L-ribitol 
• 117858-82-9 (2S,3S,4R)-N-benzyl-2-hydroxymethyl-3,4-O-isopropylidenepyrrolidine-3,4-diol 

Relevant articles and documents

Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC: Synthesis, antibacterial properties, and docking studies

The Zn2+-dependent deacetylase LpxC is an essential enzyme in Gram-negative bacteria, which has been validated as antibacterial drug target. Herein we report the chiral-pool synthesis of novel D- and L-proline-derived 3,4-dihydroxypyrrolidine hydroxamates and compare their antibacterial and LpxC inhibitory activities with the ones of 4-monosubstituted and 3,4-unsubstituted proline derivatives. With potent antibacterial activities against several Gram-negative pathogens, the L-proline-based tertiary amine 41g ((S)-N-hydroxy-1-(4-{[4-(morpholinomethyl)phenyl]ethynyl}benzyl)pyrrolidine-2-carboxamide) was found to be the most active antibacterial compound within the investigated series, also showing some selectivity toward EcLpxC (Ki = 1.4 μM) over several human MMPs.

SYNTHESIS FROM D-MANNOSE OF 1,4-DIDEOXY-1,4-IMINO-L-RIBITOL AND OF THE α-MANNOSIDASE INHIBITOR 1,4-DIDEOXY-1,4-IMINO-D-TALITOL

The syntheses of 1,4-dideoxy-1,4-imino-L-ribitol and of 1,4-dideoxy-1,4-imino-D-talitol from D-mannose are described. 1,4-Dideoxy-1,4-imino-D-talitol is a specific and competitive inhibitor of human liver α-mannosidase in vitro and also blocks the lysosomal catabolism of asparigine-linked glycans of glycoproteins in vivo.