158895-45-5

Basic information

• Product Name: 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne
• Synonyms: 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne
• CAS NO: 158895-45-5
• Molecular Weight: 519.641
• Mol File: 158895-45-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne(158895-45-5)
• EPA Substance Registry System: 1-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl)oct-1-yne(158895-45-5)

Safety Data

• Hazardous Substances Data: 158895-45-5(Hazardous Substances Data)

Upstream product

• 59464-24-3 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-galactopyranosyl bromide 
• 113794-23-3 tributyl(oct-1-yn-1-yl)stannane 

Downstream Products

• 161254-85-9 Acetic acid (2R,3R,4R,5S,6R)-5-acetylamino-3,4-bis-benzyloxy-6-oct-1-ynyl-tetrahydro-pyran-2-ylmethyl ester 

Relevant articles and documents

Synthesis of α-Glycopyranosides of D-Galactosamine and D-Glucosamine via Iodocyclization of Corresponding Glycals and Silver Tetrafluoroboranuide-Promoted Alkynylation at the Anomeric Centre

Iodocyclization of O-stannylated D-galactal 1, followed by azide ion displacement, gave 1,6-anhydro-2-azido-2-deoxy-β-D-galactopyranose 9 in a expeditious way.Transformation into bromide 12 allowed coupling of various alkynyltributylstannanes in the presence of silver tetrafluoroboranuide (silver tetrafluoroborate), thus affording the corresponding α,β-C-(D-galactopyranosyl)alkynes 13 - 17.Application of this methodology to the D-gluco isomeric bromide 24 gave a C-(D-glucopyranosyl)octyne 25 with total α-stereoselectivity.Conventional deprotection and saturation of the acetylenic linkage led to C-octyl-α-glycopyranosides of D-galactosamine 20 and D-glucosamine 28.