51020-42-9

Basic information

• Product Name: 2,6-dideoxyhexopyranose
• CAS NO: 51020-42-9
• Molecular Formula: C₆H₁₂O₄
• Molecular Weight: 148.1571
• Mol File: 51020-42-9.mol

Chemical Properties

• Boiling Point: 320.1°C at 760 mmHg
• Flash Point: 147.4°C
• Density: 1.366g/cm³
• Vapor Pressure: 2.64E-05mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: 2,6-dideoxyhexopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dideoxyhexopyranose(51020-42-9)
• EPA Substance Registry System: 2,6-dideoxyhexopyranose(51020-42-9)

Safety Data

• Hazardous Substances Data: 51020-42-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-dideoxyhexopyranose is used as a key compound in the development of new antibiotics and bioactive compounds due to its antibacterial properties. Its unique structure allows it to interact with bacterial cells, inhibiting their growth and potentially leading to the creation of novel therapeutic agents.
Used in Cancer Research:
In cancer research, 2,6-dideoxyhexopyranose is used as a potential antitumor agent. Its ability to interfere with tumor cell growth and proliferation makes it a promising candidate for further investigation into its role in cancer treatment and prevention.
Used in Medicinal Chemistry:
2,6-dideoxyhexopyranose is utilized as a building block in the synthesis of complex molecules with potential medicinal applications. Its unique structure can be modified to create new compounds with enhanced properties, contributing to the advancement of drug discovery and development.
Used in Microbiology Research:
2,6-dideoxyhexopyranose is employed as a research tool in microbiology to study the interactions between microorganisms and their environment. Understanding how this rare sugar affects microbial growth and metabolism can provide insights into the development of new antimicrobial strategies and the exploration of microbial ecosystems.

Upstream product

• 117479-84-2 cynafoside-C 
• 98665-67-9 dregeoside H 
• 97399-97-8 cynantratoside-B 
• 97399-97-8 glaucogenin-C 3-O-α-D-oleandropyranosyl-(1→4)-β-D-digitoxopyranosyl-(1→4)-β-D-oleandropyranoside 
• 97399-99-0 cynantratoside-D 
• 71-63-6 digitoxin 
• 1111-39-3 acetyldigitoxin 
• 17575-20-1 Digitoxigenin 3-O-bisdigitoxosideacetyldigilanidobioside, or lanatoside A 

Downstream Products

• 4092-45-9 methyl 2,6-dideoxy-β-D-ribo-hexopyranoside 
• 132741-54-9 D-digitoxonic acid lactone 
• 20561-87-9 2,6-dideoxy-L-ribo-hexonic acid phenylhydrazide 
• 58341-66-5 methyl 2,6-di-O-benzyl-α-D-glucopyranoside 
• 71122-36-6 methyl 3,4-bis(O-benzoyl)-2-deoxy-α-L-fucopyranoside 
• 4092-45-9 methyl 2,6-dideoxy-α-L-lyxo-hexopyranoside 
• 1256381-68-6 C₂₁H₃₄Cl₂N₂O₄ 
• 118488-79-2 1-O-(3,5-dinitrophenylcarbamoyl)-3,4-O-isopropylidene-α-D-digitoxopyranose 
• 291282-23-0 C₃₁H₄₀O₃S₂ 
• 258348-49-1 (3S,4R,5R)-3,4,5-Tris-benzyloxy-hexanoic acid 
• 102235-57-4 3,4,5-Tri-O-benzyl-2,6-didesoxy-D-ribo-aldehydo-hexose 
• 33985-27-2 1,3,4-tri-O-acetyl-2,6-dideoxy-D-xylo-hexopyranose 

Relevant articles and documents

Three new isoflavonoid glycosides from the mangrove-derived actinomycete micromonospora aurantiaca 110B

The mangrove ecosystem is a rich resource for the discovery of actinomycetes with potential applications in pharmaceutical science. Besides the genus Streptomyces, Micromonospora is also a source of new bioactive agents. We screened Micromonospora from the rhizosphere soil of mangrove plants in Fujian province, China, and 51 strains were obtained. Among them, the extracts of 12 isolates inhibited the growth of human lung carcinoma A549 cells. Strain 110B exhibited better cytotoxic activity, and its bioactive constituents were investigated. Consequently, three new isoflavonoid glycosides, daidzein-40-(2-deoxy-a-l-fucopyranoside) (1), daidzein-7-(2-deoxy-a-l-fucopyranoside) (2), and daidzein-40,7-di-(2-deoxy-a-l-fucopyranoside) (3) were isolated from the fermentation broth of strain 110B. The structures of the new compounds were determined by spectroscopic methods, including 1D and 2D nuclear magnetic resonance (NMR) and high-resolution electrospray ionization mass spectrometry (HR-ESIMS). The result of medium-changing experiments implicated that these new compounds were microbial biotransformation products of strain M. aurantiaca 110B. The three compounds displayed moderate cytotoxic activity to the human lung carcinoma cell line A549, hepatocellular liver carcinoma cell line HepG2, and the human colon tumor cell line HCT116, whereas none of them showed antifungal or antibacterial activities.

Cytotoxicity of pregnane glycosides of Cynanchum otophyllum

Fourteen new pregnane glycosides, including nine caudatin glycosides (1-9), three qinyangshengenin glycosides (10-12), one kidjoranin glycosides (13) and one gagaminin glycosides (14), along with twelve known analogs (15-26) were isolated from roots of Cy

Neuroprotective polyhydroxypregnane glycosides from Cynanchum otophyllum

Five new polyhydroxypregnane glycosides, namely cynanotosides A-E (1-5), together with two known analogues, deacetylmetaplexigenin (6) and cynotophylloside H (7), were isolated from the roots of Cynanchum otophyllum. Their structures were established by spectroscopic methods and acid hydrolysis. The neuroprotective effects of compounds 1-7 against glutamate-, hydrogen peroxide-, and homocysteic acid (HCA)-induced cell death were tested by MTT assay in a hippocampal neuronal cell line HT22. Compounds 1, 2, and 7 exhibited protective activity against HCA-induced cell death in a dose-dependent manner ranging from 1 to 30 μM, which may explain the Traditional Chinese Medicine (TCM) use of this plant for the treatment of epilepsy.

Identification of new qingyangshengenin and caudatin glycosides from the roots of Cynanchum otophyllum

HPLC analysis of the roots of Cynanchum otophyllum Scheind (Asclepiadaceae) led to the isolation of six new pregnane glycosides, specifically otophyllosides N-P (2-4) and otophyllosides Q-S (7-9), in addition to the identification of three known C-21 steroidal glycosides, otophylloside A (1), otophylloside B (5) and caudatin 3-O-β-d-glucopyranosyl-(1→4)-β- d-oleandropyranosyl-(1→4)-β-d-cymaropyranosyl-(1→4) -β-d-cymaropyranoside (6). The structure of each glycoside was determined by detailed spectroscopic analysis and chemical methods. All compounds contain qingyangshengenin or caudatin aglycones and a straight sugar chain consisting of 4-7 hexosyl moieties with the mode of 1→4 linkage. The optically isomeric monosaccharides, d- and l-cymarose, coexisted in both otophyllosides R (8) and S (9).

Steroidal glycosides from the aerial part of Asclepias incarnata

The aerial part of Asclepias incarnata afforded 34 pregnane glycosides. These were confirmed to have lineolon, isolineolon, ikemagenin, 12-O- nicotinoyllineolon, deacylmetaplexigenin, metaplexigenin, rostratamine, 12-O- acetyllineolon, 15β-hydroxylineolon

Corchorusosides A, B, C, D, and E, new cardiotonic oligoglycosides from the seeds of Corchorus olitorius L. (Moroheiya)

The methanolic extract of the seeds of Corchorus olitorius L. (Moroheiya) was found to show inhibitory effect against Na+,K+-ATPase and positive inotropic activity in the guinea pig isolated atria. Through bioassay-guided separation from the methanolic extract, new cardenolide oligoglycosides called corchorusosides A, B, C, D, and E were isolated together with six known cardenolide oligoglycosides. The structures of new corchorusosides were determined on the basis of chemical and physicochemical evidence. All cardenolide oligoglycosides from the seeds showed potent inhibitory activity against Na+,K+-ATPase, which was equivalent to those of digitoxin and ouabain. The methanolic extract, glycoside fraction, and principal glycoside showed potent acute toxicity by intraperitoneal administration, whereas they showed little acute toxicity by oral administration. Furthermore, by means of HPLC quantitative analysis of the cardiotonic oligoglycosides, it was found that the glycosides mainly distributed in the seeds , while the edible parts such as fresh young leaves and stems contained only trace amount.

Thermal Degradation of Glycosides, VI - Hydrothermolysis of Cardenolide and Flavonoid Glycosides

The hydrothermolysis of cardenolide and flavonoid glycosides is described.On heating with water or water/dioxane, cardenolide (1, 5, 11) and flavonoid glycosides (16, 20, 23, 27) are converted into their genuine aglycones and partially hydrolyzed products, together with saccharide components.Meanwhile, the glycosidic linkage of 2-deoxy sugar moieties in cardenolide glycosides is more readily cleaved than that of the common sugar moieties by means of hydrothermolysis.Therefore, hydrothermolysis of the uzarigenin triglycoside (13), bearing a 2-deoxy sugar moiety whichis directly attached to the aglycone, leads to selective cleavage of the sugar-aglycone linkage.The hydrothermolyzed products have been isolated by chromatography and their structures elucidated by spectroscopic methods. Key Words: Thermolysis / Degradation, thermal / Carbohydrates / Glycosides / Cardenolides / Steroids / Flavonoids

CARDIAC GLYCOSIDES OF ERYSIMUM CONTRACTUM

The cardenolide composition of Erysimum contractum Somm. et Lew. familiy Brassicaceae (Cruciferae) has been investigated.The seeds of this plant have yielded strophanthidin, erysimin, erysimoside, erycordin, and new cardiac glycoside which has been called nigrescigenin digitoxoside.It has mp 141 - 145 deg C, D20 +16.0 +/- 2 deg C (c 0.75; methanol), C29H42O10.On the basis of chemical transformations and spectral investigations it has been established that the new glycoside is 3β-D-digitoxopyranosyloxy-5,11α,14-trihydroxy-19-oxo-5β,14β-card-20(22)-enolide.The total content of cardiac glycosides in the seeds of this plant amounted to 3.2percent, including 1.26percent of erysimoside.

Cyclopentenoid cyanohydrin glycosides with unusual sugar residues.

The cyclopentenoid cyanohydrin glycosides passicapsin and passibiflorin have been identified as (1S, 4R)-1-(beta-D-glucopyranosyloxy)-4-(2,6-dideoxy-beta-D-xylo-hex o pyranosyloxy)-2-cyclopentene-1-carbonitrile and (1S, 4R)-1-(beta-D-glucopyranosyloxy)-4-(6-deoxy-beta-D-gulopyranosy loxy)-2- cyclopentene-1-carbonitrile, respectively, using one- and two-dimensional NMR spectroscopy, selective acid-catalysed cleavage of the glycosidic linkages of the deoxy sugars, and optical rotation data.