347838-02-2

Basic information

• Product Name: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate
• Synonyms: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate
• CAS NO: 347838-02-2
• Molecular Weight: 646.507
• Mol File: 347838-02-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate(347838-02-2)
• EPA Substance Registry System: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate(347838-02-2)

Safety Data

• Hazardous Substances Data: 347838-02-2(Hazardous Substances Data)

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 

Downstream Products

• 347838-09-9 1,2;3,4-di-O-isopropylidene-6-O-[methyl (4,7,8,9-tetra-O-acetyl-5-N-acetylacetamido-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosyl)onate]-α-D-galactopyranose 
• 347838-05-5 1,2,3,4-di-O-isopropylidene-6-O-[methyl [5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-3-phenylseleno-D-erythro-β-L-gluco-2-nonulopyranosyl]onate]-α-D-galactopyranose 
• 347838-08-8 methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-2-O-(diethyl phosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate 
• 347838-06-6 methyl 4,7,8,9-tetra-O-acetyl-5-(N-acetylacetamido)-3,5-dideoxy-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate 
• 347838-04-4 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-(diethylphosphite)-3-phenylseleno-D-erythro-α-L-gluco-2-nonulopyranosonate 

Relevant articles and documents

A study of the donor properties of sialyl phosphites having an auxiliary 3-(S)-phenylseleno group

Two phosphite sialyl donors, each having an auxiliary 3-(S)-phenylseleno group, were prepared and evaluated. The phenylseleno group was introduced via a new mode of generating phenylselenenic acid ('PhSeOH'). Although the sialyl donors provided fair yields (32-76%) of the desired sialosides in glycosylations of the reactive acceptor 1,2;3,4-di-O-isopropylidene-α-D-galactopyranose, no sialylated products could be obtained with less reactive acceptors. The presence of a 5-N-acetylacetamido group on the phosphite sialyl donor did not appear to improve its sialylating capability. The weak C-Se bond, possibly in combination with a steric hindrance, which disfavors α-nitrilium ion formation, seem to explain the unsuccessful sialylations of the less reactive acceptors.