854911-48-1

Basic information

• Product Name: 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride
• Synonyms: 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride
• CAS NO: 854911-48-1
• Molecular Weight: 533.553
• Mol File: 854911-48-1.mol

Chemical Properties

• CAS DataBase Reference: 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride(854911-48-1)
• EPA Substance Registry System: 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl fluoride(854911-48-1)

Safety Data

• Hazardous Substances Data: 854911-48-1(Hazardous Substances Data)

Upstream product

• 854911-33-4 ethyl 3,6-di-O-benzyl-2-deoxy-4-O-mesyl-2-phthalimido-1-thio-β-D-glucopyranoside 
• 115533-35-2 ethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 159734-70-0 phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 865096-52-2 phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 
• 190247-77-9 ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 
• 865096-51-1 phenyl 3,6-di-O-benzyl-2-deoxy-4-O-methanesulfonyl-2-phthalimido-1-thio-β-D-glucopyranoside 

Downstream Products

• 865096-54-4 phenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 865096-53-3 phenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 

Relevant articles and documents

Synthesis of sulfated phenyl 2-acetamido-2-deoxy-D-galactopyranosides. 4-O-Sulfated phenyl 2-acetamido-2-deoxy-β-D-galactopyranoside is a competitive acceptor that decreases sulfation of chondroitin sulfate by N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase

We have previously cloned N-acetylgalactosamine 4-sulfate 6-O-sulfotransferase (GalNAc4S-6ST), which transfers sulfate from 3′-phosphoadenosine 5′-phosphosulfate (PAPS) to the C-6 hydroxyl group of the GalNAc 4-sulfate residue of chondroitin sulfate A and forms chondroitin sulfate E containing GlcA-GalNAc(4,6-SO4) repeating units. To investigate the function of chondroitin sulfate E, the development of specific inhibitors of GalNAc4S-6ST is important. Because GalNAc4S-6ST requires a sulfate group attached to the C-4 hydroxyl group of the GalNAc residue as the acceptor, the sulfated GalNAc residue is expected to interact with GalNAc4S-6ST and affect its activity. In this study, we synthesized phenyl α- or -β-2-acetamido-2-deoxy-β-D-galactopyranosides containing a sulfate group at the C-3, C-4, or C-6 hydroxyl groups and examined their inhibitory activity against recombinant GalNAc4S-6ST. We found that phenyl β-GalNAc(4SO4) inhibits GalNAc4S-6ST competitively and also serves as an acceptor. The sulfated product derived from phenyl β-GalNAc(4SO4) was identical to phenyl β-GalNAc(4,6-SO 4). These observations indicate that derivatives of β-D-GalNAc(4SO4) are possible specific inhibitors of GalNAc4S-6ST.

Synthesis of 2-amino-2-deoxy-β-D-galactopyranosyl-(1→4)-2-amino- 2-deoxy-β-D-galactopyranosides: Using various 2-deoxy-2-phthalimido-D- galactopyranosyl donors and acceptors

A systematic study is presented of the efficiency of the most common glycosylation methods using standard 2-deoxy-2-phthalimidogalactopyranosyl donors ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D- galactopyranoside (3a), 4-O-Acetyl-3,