13479-66-8

Basic information

• Product Name: alpha-d-Glucopyranoside, methyl 3,4,6-tri-O-methyl-
• Synonyms: alpha-d-Glucopyranoside, methyl 3,4,6-tri-O-methyl-;Methyl 3-O,4-O,6-O-trimethyl-α-D-glucopyranoside
• CAS NO: 13479-66-8
• Molecular Formula: C₁₀H₂₀O₆
• Molecular Weight: 236.26
• Mol File: 13479-66-8.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: alpha-d-Glucopyranoside, methyl 3,4,6-tri-O-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-d-Glucopyranoside, methyl 3,4,6-tri-O-methyl-(13479-66-8)
• EPA Substance Registry System: alpha-d-Glucopyranoside, methyl 3,4,6-tri-O-methyl-(13479-66-8)

Safety Data

• Hazardous Substances Data: 13479-66-8(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 6893-57-8 methyl-(di-O-methyl-2,3-anhydro-β-D-allopyranoside) 
• 116237-66-2 C₇₇H₁₃₀N₂O₂₆ 
• 128503-59-3 methyl 2-O-benzyl-3,4,6-tri-O-methyl-β-D-glucopyranoside 
• 102902-46-5 licorice-saponin C2 
• 16740-98-0 tri-O-methyl-D-glucal 
• 118525-44-3 C₄₅H₆₈O₁₅ 
• 74-88-4 methyl iodide 
• 129297-27-4 cycloaraloside C nona-O-methylether 
• 1455-13-6 deuteromethanol 
• 908576-11-4 methyl-[O³,O⁴,O⁶-trimethyl-O²-(toluene-4-β-D-sulfonyl)-glucopyranoside] 
• 82793-05-3 3-O-[α-L-rhamnopyranosyl(1->2)-β-D-glucopyranosyl(1->2)-β-D-glucuronopyranosyl]olean-12-en-3β,22β,24-triol 
• 911652-40-9 methyl-(O²-benzyl-O³-methyl-β-D-glucopyranoside) 

Downstream Products

• 34327-07-6 3,4,6-tri-O-methyl-D-glucose 

Relevant articles and documents

Triterpene and steroidal glycosides of the genus Melilotus and their genins. VI. Melilotoside A2 and adzukisaponin v from the roots of M. tauricus

Two triterpene glycosides of the oleanane series, melilotoside A 2 and previously known adzukisaponin V, were isolated from the roots of Melilotus tauricus (L.) Pall. (Fabaceae). The structures of the glycosides were proved based on chemical transformations. Melilotoside A2 had the structure soyasapogenol B 3-O-β-D-glucouronopyranoside; adzukisaponin V, soyasapogenol B 3-O-[α-L-rhamnopyranosyl-(1-2)-β-Dglucopyranosyl- (1-2)-β-D-glucuronopyranoside].

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

Naphthyl 3,4,6-tri-O-methyl-β-D-glucopyranoside as a chiral auxiliary in an asymmetric 1,4-addition reaction

Naphthyl 3,4,6-tri-O-methyl-β-D-glucopyranoside, easily synthesized from tri-O-acetyl-D-glucal, has been applied as a chiral auxiliary in an asymmetric Michael addition to the 2-O-crotonate. A very high facial diastereoselection (>95%) was obtained. No diastereoselection was observed when 1,3,4,6-tetra-O-methyl-β-D-glucopyranoside was used as the chiral auxiliary. A stereochemical model, taking into account steric shielding and π-stacking effects, is proposed on the basis of the observed results.