484-36-6

Basic information

• Product Name: methyl 6-deoxy-3-O-D-glucopyranose
• CAS NO: 484-36-6
• Molecular Weight: 178.185
• Mol File: 484-36-6.mol

Chemical Properties

• CAS DataBase Reference: methyl 6-deoxy-3-O-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-deoxy-3-O-D-glucopyranose(484-36-6)
• EPA Substance Registry System: methyl 6-deoxy-3-O-D-glucopyranose(484-36-6)

Safety Data

• Hazardous Substances Data: 484-36-6(Hazardous Substances Data)

Upstream product

• 119902-15-7 Δ⁵-pregnene 3β,17α,20(S)-triol 20-O-β-D-digitalopyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-canoropyranosyl-(1->4)-β-D-digitoxopyranosyl-(1->5)-3,7-dideoxy-4-O-methyl-α-D-gluco-2-heptulopyranosyl-(2-4)-dideoxy-(1->3)-β-D-canaropyranoside 
• 119902-17-9 Δ⁵-pregnene-3β,17α,20(S)-triol 20-O-(β-D-digitalopyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-cymaropyranosyl-(1->4)-β-D-cymaropyranosyl-(1->5)-3,7-dideoxy-4-O-methyl-α-D-gluco-2-heptulopyranosyl-(2-4)-dideoxy-(1->3)-β-D-canaropyranoside) 
• 18810-25-8 3β-O-(β-D-digitalosyl)-14-hydroxy-5β,14β-card-20(22)-enolide 
• 14364-89-7 Gitoxigenin 3-O-monodigitalosideglucoside, or digitalinum verum 

Downstream Products

• 112047-81-1 O³-methyl-D-lyxo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 1393730-59-0 2,4-di-O-benzoyl-β-D-thevetopyranosyl benzoate 
• 1393730-43-2 2,4-di-O-benzoyl-α-D-thevetopyranosyl benzoate 

Relevant articles and documents

New pregnane glycoside derivative from Caralluma retrospiciens (Ehrenb)

Retrospinoside (1) is a new polyoxy pregnane glycoside which was isolated and characterised from the aerial parts of Caralluma retrospiciens (Ehrenb.) N. E. Br., family Apocynaceae. The structure was established as 3-O-[β-D-glucopyranosyl-(1 → 4)-β-D-(3-O-methyl-6-desoxygalactopyranosy)]-14,15,20-trihydroxy-4β-pregnane. Its structural elucidation was performed through extensive spectroscopic measurements including 1D- and 2D-NMR, and HRMS, in addition to chemical methods.

Five new pregnane glycosides from Gymnema sylvestre and their α-glucosidase and &alphla;-amylase inhibitory activities

Gymnema sylvestre, a medicinal plant, has been used in Indian ayurvedic traditional medicine for the treatment of diabetes. Phytochemical investigation of Gymnema sylvestre led to the isolation of five new pregnane glycosides, gymsylosides A-E (1-5) and four known oleanane saponins, 3β-O-β-D-glucopyranosyl (1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (6), gymnemoside-W1 (7), 3β-O-β-D-xylopyranosyl-(1→6)-β-Dglucopyranosyl-(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester (8), and alternoside XIX (9). Their structures were identified based on spectroscopic evidence and comparison with those reported in the literature. All compounds were evaluated for their α-glucosidase and α-amylase inhibitory activities. Compounds 2-4 showed significant α-amylase inhibitory activity, with IC50 values ranging from 113.0 to 176.2 μM.

New pregnane glycosides from Caralluma hexagona Lavranos and their in vitro α-glucosidase and pancreatic lipase inhibitory effects

Three new pregnane glycosides in addition to four known compounds were isolated from the methylene chloride fraction of Caralluma hexagona Lavranos using bioassay-guided fractionation. The new compounds were identified as 12,20-di-O-benzoyl-3β,8β,12β,14β,20-pentahydroxy-(20R)-pregn-5-ene-3-O-β-D-glucopyranosyl-(1→4)-β-D-digitaloside (1), 3β,8β,14β,20-tetrahydroxy (20R)-pregn-5-ene-3-O-β-D-glucopyranosyl-(1→4)-O-β-D-digitaloside-20-O-β–D-glucopyranoside (2), 3β,8β,14β,20-tetrahydroxy-(20R)-pregn-5-ene-3-O-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl-(1→4)-O-β-D-digitaloside-20-O-β–D-glucopyranoside (3), along with the known compounds luteolin 4`-O-neohesperidoside (4), apigenin-8-C-neohesperoside (5), β-sitosterol (6) and β-sitosterol glucoside (7). Preliminary studies of the crude methanolic extract and methylene chloride fraction showed inhibitory effects against α-glucosidase and pancreatic lipase. Among the isolated compounds, compound 5 showed the most potent α-glucosidase inhibition with IC50 value of 0.82 ± 2.50 μM compared to acarbose (0.81 ± 0.86 μM). Whereas compound 1 showed the highest inhibitory activity on pancreatic lipase with an IC50 value of 23.59 ± 2.49 μM compared to orlistat (7.41 ± 2.26 μM).

Two new steroidal saponins from the roots of Cynanchum limprichtii

As a part of our continuing research for bioactive constituents from Cynanchum limprichtii Schltr., two new C21 steroidal glycosides limproside A (1) and limproside B (2) were isolated from the roots of Cynanchum limprichtii. Their structures were elucidated on the basis of 1D- and 2D-NMR spectroscopic data as well as HR-ESI-MS analysis. The cytotoxicity of two compounds against two selected human cancer cell lines was assayed.

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