107573-28-4

Basic information

• Product Name: 2,6-anhydro-3-deoxyoctonate
• Synonyms: 2,6-anhydro-3-deoxyoctonate
• CAS NO: 107573-28-4
• Molecular Formula: C8H14O8
• Molecular Weight: 238.19196
• Mol File: 107573-28-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 551.5°C at 760 mmHg
• Flash Point: 223.6°C
• Appearance: /
• Density: 1.769g/cm³
• Vapor Pressure: 1.85E-14mmHg at 25°C
• Refractive Index: 1.632
• CAS DataBase Reference: 2,6-anhydro-3-deoxyoctonate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-anhydro-3-deoxyoctonate(107573-28-4)
• EPA Substance Registry System: 2,6-anhydro-3-deoxyoctonate(107573-28-4)

Safety Data

• Hazardous Substances Data: 107573-28-4(Hazardous Substances Data)

Usage

General Description

2,6-anhydro-3-deoxyoctonate is a chemical compound that belongs to the family of octonic acids. This molecule is an important intermediate in the biosynthesis pathway of certain bacteria, specifically in the production of lipopolysaccharides, which are crucial for the outer membrane of gram-negative bacteria. Additionally, 2,6-anhydro-3-deoxyoctonate is also a key component in the creation of the cell wall of these bacteria. 2,6-anhydro-3-deoxyoctonate plays a significant role in the structural integrity and function of gram-negative bacteria, making it an important target for research in the development of new antibiotics and antimicrobial agents.

InChI:InChI=1/C8H14O8/c9-2-3-5(12)6(13)7(14)8(15,16-3)1-4(10)11/h3,5-7,9,12-15H,1-2H2,(H,10,11)/t3-,5-,6+,7+,8?/m1/s1

Upstream product

• 256343-21-2 [2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran 
• 171411-67-9 [2S,3R,4S,6S]-6-(tert-butyldiphenylsilyloxymethyl)-3-hydroxy-4-phenylsulfonyl-2-(2-thiopyridyl)tetrahydro-2H-pyran 
• 171411-70-4 [1S,3S,5S,6S]-3-(tert-butyldiphenylsilyloxymethyl)-9-oxo-5-phenylsulfonyl-2,7-dioxabicyclo[4.3.0]nonane 
• 256343-23-4 (3aS,5S,7S,7aS)-7-Benzenesulfonyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,2-b]pyran-3-one 
• 171411-65-7 [2S,4S]-2-(tert-butyldiphenylsilyloxymethyl)-4-phenylsulfonyl-3,4-dihydro-2H-pyran 
• 171411-71-5 [4S,6S,1'R]-2-(tert-butyldiphenylsilyloxymethyl)-6-(1,2-dihydroxyethyl)-3,6-dihydro-2H-pyran 
• 109150-74-5 methyl [2R,3S,4R,6S,1'R]-3,4-isopropylidenedioxy-2-[(1,2-isopropylidenedioxy)ethyl]tetrahydroo-2H-pyran-6-carboxylate 
• 107961-77-3 methyl 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-galacto-octonate 
• 114474-86-1 [2R,3S,4R,6S,1'R]-3,4-isopropylidenedioxy-2-[(1,2-isopropylidenedioxy)ethyl]tetrahydro-2H-pyran-6-carboxylic acid 
• 114474-75-8 2,6-anhydro-3-deoxy-4,5:7,8-di-O-isopropylidene-D-glycero-D-talo-octitol 
• 106174-63-4 methyl 2,6-anhydro-3-deoxy-D-glycero-D-talo-octonate 
• 226226-37-5 C₂₆H₂₈O₉ 

Downstream Products

• 137040-52-9 (R)-4-Carbamoyl-4-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-butyric acid benzyl ester 
• 137040-56-3 (S)-6-Benzyloxycarbonylamino-2-((R)-4-benzyloxycarbonyl-4-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-butyrylamino)-hexanoic acid benzyl ester 
• 137040-54-1 (S)-6-Benzyloxycarbonylamino-2-[(R)-4-benzyloxycarbonyl-4-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-butyrylamino]-hexanoic acid benzyl ester 
• 137040-55-2 (R)-4-[(S)-5-Benzyloxycarbonylamino-1-((R)-1-benzyloxycarbonyl-ethylcarbamoyl)-pentylcarbamoyl]-2-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-butyric acid benzyl ester 
• 137040-53-0 (R)-2-((S)-2-{[(2S,4R,5R,6R)-6-((R)-1,2-Dihydroxy-ethyl)-4,5-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-propionylamino)-pentanedioic acid dibenzyl ester 

Relevant articles and documents

Template-directed intramolecular C-glycosidation. Formation of tetrahydrofurans and application to the synthesis of a higher-order sugar

Cation-mediated cyclisation reactions of silyl enol ether-containing thioglycosides give bicyclic ketotetrahydrofurans. Cyclisation of an analogous 3-phenyl-2-propenyl ether-containing substrate gives an intermediate in the total synthesis of the higher-order sugar 2,3-dideoxy-D- manno-2-octulopyranosonic acid.

Template-directed intramolecular C-glycosidation. Total synthesis of 2,3-dideoxy-D-manno-2-octulopyranosonic acid

The total synthesis of the KDO-inhibitor 2,3-dideoxy-D-manno-2-octulopyranosonic acid (2-deoxy-KDO) starting from TBDPS-protected (S)-glycidol and 3,3-dimethoxy-1-(phenylsulfonyl)-propane is described. The key steps are silver(I) trifluoromethylsulfonate-