194149-26-3

Basic information

• Product Name: methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside
• Synonyms: methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside
• CAS NO: 194149-26-3
• Molecular Weight: 370.402
• Mol File: 194149-26-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside(194149-26-3)
• EPA Substance Registry System: methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside(194149-26-3)

Safety Data

• Hazardous Substances Data: 194149-26-3(Hazardous Substances Data)

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 

Downstream Products

• 1340474-17-0 (Z)-1-(2-phenyl-4H-1,3-dioxin-6-yl)-3-(phenylamino)prop-2-en-1-one 
• 1340474-18-1 (Z)-1-(2-phenyl-4H-1,3-dioxin-6-yl)-3-(p-tolylamino)prop-2-en-1-one 
• 1340474-19-2 (Z)-3-(4-ethylphenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 1340474-20-5 (Z)-3-(4-ethoxyphenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 1340474-21-6 (Z)-3-(2-methoxyphenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 1340474-22-7 (Z)-1-(2-phenyl-4H-1,3-dioxin-6-yl)-3-(m-tolylamino)prop-2-en-1-one 
• 1340474-23-8 (Z)-3-(4-bromophenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 1340474-24-9 (Z)-3-(3,4-dimethoxyphenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 1340474-25-0 (Z)-3-(4-morpholinophenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 1340474-16-9 (Z)-3-(4-methoxyphenylamino)-1-(2-phenyl-4H-1,3-dioxin-6-yl)prop-2-en-1-one 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 195875-44-6 methyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 911484-78-1 methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-deoxy-6-thio-α-D-mannopyranoside 
• 65518-53-8 methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside 

Relevant articles and documents

Glycosylation catalyzed by a chiral bronsted acid

"Chemical equation presented" The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochem

Organocatalysis for the acid-free O-arylidenation of carbohydrates

Methyl glycopyranosides of glucose, galactose, and mannose, their 2,3-di-O-benzyl-protected derivatives, as well as the unprotected sugars react with p-methoxybenzaldehyde dimethyl acetal (3) and with benzaldehyde dimethyl acetal (7) as reagents in the presence of thiourea 1 or squaramide 2 as the organocatalyst to afford regioselectively 4,6-O-arylidenated derivatives 5 and 8. With an excess amount of 3 or 7, diarylidenated derivatives are also obtained. In situ formation of acetals of type 3 and 7 from corresponding aldehydes 10 and 13 in the presence of an orthoester and organocatalyst 1 or 2 can be used to generate 5 and 8 directly from the aldehydes. Some substrates also lead to mixed orthoesters with this procedure. The reaction courses are discussed. A squaramide catalyzes the 4,6-O-arylidenation of glucose, mannose, and galactose with the use of arenecarbaldehyde dimethyl acetals or arenecarbaldehydes and orthoesters as the reagents. Glycoside derivatives also undergo this reaction. Copyright

Base-promoted reaction of methyl 4,6-O-benzylidene-3-deoxy-hexopyranosid-2- ulose and various arylamines

Reaction of methyl 4,6-O-benzylidene-3(2)-deoxy-hexopyranosid-2(3)-ulose (1) with various arylamines under Bargellini reaction conditions was investigated. A series of unique enaminoketones 3-12 was obtained unexpectedly under basic conditions in 52-72% y