69247-23-0

Basic information

• Product Name: 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• CAS NO: 69247-23-0
• Molecular Weight: 472.489
• Mol File: 69247-23-0.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(69247-23-0)
• EPA Substance Registry System: 6-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)1,2:3,4-di-O-isopropylidene-α-D-galactopyranose(69247-23-0)

Safety Data

• Hazardous Substances Data: 69247-23-0(Hazardous Substances Data)

Upstream product

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 2873-29-2 D-glucal triacetate 
• 2873-29-2 3,4,6-tri-O-acetyl-D-glucal 
• 286410-13-7 phenyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-1-thio-hex-2-enopyranoside 
• 136787-43-4 4,6-di-O-acetyl-1,5-anhydro-2-deoxy-3-S-phenyl-3-thio-D-ribo-hex-1-enitol 
• 4098-06-0 triacetyl-D-galactal 

Relevant articles and documents

Palladium-Catalyzed α-Stereoselective O-Glycosylation of O(3)-Acylated Glycals

Pd(MeCN)2Cl2 enables the α-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to preactivate either donor or nucleophile. Mechanistic studies suggest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium intermediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with the synthesis of a range of glycosides and glycoconjugates of synthetic utility.

Substrate-Controlled Direct α-Stereoselective Synthesis of Deoxyglycosides from Glycals Using B(C6F5)3 as Catalyst

B(C6F5)3 enables the metal-free unprecedented substrate-controlled direct α-stereoselective synthesis of deoxyglycosides from glycals. 2,3-Unsaturated α-O-glycoside products are obtained with deactivated glycals at 75 °C in the presence of the catalyst, while 2-deoxyglycosides are formed using activated glycals that bear no leaving group at C-3 at lower temperatures. The reaction proceeds in good to excellent yields via concomitant borane activation of glycal donor and nucleophile acceptor. The method is exemplified with the synthesis of a series of rare and biologically relevant glycoside analogues.

Gd(OTf)3 catalyzed preparation of 2,3-unsaturated O-, S-, N-, and C-pyranosides from glycals by Ferrier Rearrangement

By using Gd(OTf)3 as the catalyst, synthesis of 2,3-unsaturated-glycosides has been performed by Ferrier Rearrangement. A series of 2,3-unsaturated O-, S-, N-, and C-glycosides were obtained from 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-benzyl-d-glucal, and 3,4-di-O-acetyl-l-rhamnal under mild reaction conditions in good yields and high anomeric selectivities.