1416134-63-8

Basic information

• Product Name: methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate
• Synonyms: methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate;(2S,5R)-7-Oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid ethyl ester
• CAS NO: 1416134-63-8
• Molecular Formula: C₁₆H₂₀N₂O₄
• Molecular Weight: 290.31442
• EINECS: -0
• Mol File: 1416134-63-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate(1416134-63-8)
• EPA Substance Registry System: methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate(1416134-63-8)

Safety Data

• Hazardous Substances Data: 1416134-63-8(Hazardous Substances Data)

Usage

General Description

Methyl (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate is a chemical compound consisting of a methyl group and a carboxylate group attached to a complex central structure. The central structure is a diazabicyclo[3.2.1]octane ring system with a benzyloxy group attached. The compound is a chiral molecule, with two stereocenters at the 2nd and 5th positions. It is commonly utilized in the synthesis of pharmaceuticals and agrochemicals due to its unique structural and functional properties. Additionally, the compound may also possess biological activities that are of interest for research and development purposes.

Upstream product

• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 695183-75-6 (2S,5S)-5-hydroxypiperidin-2-carboxylic acid methyl ester 
• 63088-78-8 (2S,5R)-5-hydroxypiperidine-2-carboxylic acid 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1463501-46-3 (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 1463501-45-2 (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-(2-nitrophenyl)sulfonamido)piperidine-1,2-dicarboxylate 
• 77925-80-5 N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 208519-98-6 (S)-ethyl 2-(((tert-butoxy)carbonyl)amino)-6-diazo-5-oxohexanoate 
• 1416134-47-8 (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate 
• 1416134-60-5 5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester 
• 1416134-59-2 C₂₀H₂₉ClN₂O₅ 
• 1416134-58-1 ethyl (S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ⁶-sulfanylidene)-5-oxohexanoate 
• 1171080-45-7 (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 

Downstream Products

• 1192500-31-4 (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate 
• 1192651-49-2 (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192491-61-4 (2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt 
• 1192651-80-1 ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt 
• 1471297-60-5 (2S,5R)-2-(5-amino-1,2,4-oxadiazol-3-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471297-86-5 (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1471297-88-7 (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471298-01-7 (2S,5R)-2-(3-amino-1,2,4-oxadiazol-5-yl)-6-(benzyloxy)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471298-12-0 tert-butyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate 
• 1471298-14-2 (2S,5R)-6-(benzyloxy)-2-(3-(piperidin-4-yl)-1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471298-16-4 (9H-fluoren-9-yl)methyl 4-(5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate 
• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 1463501-48-5 (2S,5R)-6-(benzyloxy)-2-(hydroxymethyl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1463501-50-9 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbaldehyde 

Relevant articles and documents

Discovery of ANT3310, a Novel Broad-Spectrum Serine β-Lactamase Inhibitor of the Diazabicyclooctane Class, Which Strongly Potentiates Meropenem Activity against Carbapenem-Resistant Enterobacterales and Acinetobacter baumannii

The diazabicyclooctanes (DBOs) are a class of serine β-lactamase (SBL) inhibitors that use a strained urea moiety as the warhead to react with the active serine residue in the active site of SBLs. The first in-class drug, avibactam, as well as several other recently approved DBOs (e.g., relebactam) or those in clinical development (e.g., nacubactam and zidebactam) potentiate activity of β-lactam antibiotics, to various extents, against carbapenem-resistant Enterobacterales (CRE) carrying class A, C, and D SBLs; however, none of these are able to rescue the activity of β-lactam antibiotics against carbapenem-resistant Acinetobacter baumannii (CRAB), a WHO "critical priority pathogen"producing class D OXA-type SBLs. Herein, we describe the chemical optimization and resulting structure-activity relationship, leading to the discovery of a novel DBO, ANT3310, which uniquely has a fluorine atom replacing the carboxamide and stands apart from the current DBOs in restoring carbapenem activity against OXA-CRAB as well as SBL-carrying CRE pathogens.

Preparation method of avibactam sodium

The invention discloses a synthesis method of avibactam sodium. (2S,5R)-benzyloxyamino piperidine-2-ethyl formate oxalate (I) is used as an initial raw material; and the method comprises the followingsteps: reacting the raw material with a protecting group, carrying out carbonylation cyclization, carrying out hydrolysis of ester, ammoniating, sulfonating with a sulfur trioxide complex, salifyingwith an ammonium ion source, and salifying with a sodium salt to obtain avibactam sodium, and has the advantages of simple operation, easily controlled conditions, easy industrial production and wideapplication prospect.

Production method for diazabicyclooctane derivative and intermediary body thereof

The present invention provides a production method for a diazabicyclooctane derivative expressed by formula (IV), and an intermediary body thereof (in the formula: P is an acid-removable NH protective group; R1 represents a 2, 5-dioxopyrrolidine-1-yl, a 1, 3-dioxo-3a, a 4, 7, 7a-tetrahydro-1H-isoindole-2(3H)-yl, a 1, 3-dioxohexahydro-1H-isoindole-2(3H)-yl, or a 3, 5-dioxo-4-azatricyclo[5.2.1.02, 6]deca-8-en-4-yl; R2 represents hydrogen, C1CO-, or C13COCO-, R3 represents a C1-6 alkyl or a heterocyclyl, or joins with a bonded -O-NH- to form a 3-7 member heterocyclyl ring; and OBn represents a benzyloxy).