503830-93-1

Basic information

• Product Name: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• Synonyms: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS NO: 503830-93-1
• Molecular Weight: 954.116
• Mol File: 503830-93-1.mol

Chemical Properties

• CAS DataBase Reference: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside(503830-93-1)
• EPA Substance Registry System: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside(503830-93-1)

Safety Data

• Hazardous Substances Data: 503830-93-1(Hazardous Substances Data)

Upstream product

• 144914-16-9 tert-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 

Downstream Products

• 503831-00-3 N-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,4aR,6S,7R,8S,8aS)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-hydroxy-tetrahydro-pyran-3-yl]-2,2,2-trichloro-acetamide 
• 503830-99-7 tert-butyldiphenylsilyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 503830-98-6 tert-butyldiphenylsilyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-2-amino-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 503830-96-4 tert-butyldiphenylsilyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 503831-01-4 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-α-D-glucopyranosyl fluoride 
• 503830-94-2 tert-butyldiphenylsilyl 4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Solid-phase synthesis of core 2 O-linked glycopeptide and its enzymatic sialylation

The core 2-type tetrasaccharide building blocks (1a/1b) for solid-phase synthesis of glycopeptide were synthesized via stereoselective glycosylation of the disaccharyl Ser/Thr (3a/3b) with a glycosyl fluoride (2) carrying the 2-trichloroacetamido group that was readily converted into a 2-acetamido group by reduction. A segment of glycoprotein leukosialin (215-224) was synthesized by the solid-phase protocol, the building block (1b) being utilized. Cleavage of the synthetic glycopeptide from resin was effected with reagent K and subsequent treatment of the product with a cocktail for the 'low-acidity TfOH' facilitated complete removal of the benzyl groups with minimum loss of glycosidic linkages. To the deprotected glycopeptide (21), were enzymatically introduced N-acetylneuraminic acid (sialic acid) residues in remarkably high efficiency by using the specific sialyltransferases.

Preparation of core 2 type tetrasaccharide carrying decapeptide by benzyl protection-based solid-phase synthesis strategy

β-D-Gal-(1→4)-β-D-GlcNAc-[β-D-Gal-(1→3)] -α-D-GalNAc-(1→3)-L-Ser/Thr building blocks for solid-phase synthesis of glycopeptide were stereoselectively synthesized in a benzyl-protected form. The key glycosylation reaction to form β-D-GlcNAc linkage was established by the use of protected N-trichloroacetyl-D-lactosaminyl fluoride. Usefulness of the building block was demonstrated by solid-phase synthesis of a segment of human leukosialin. Benzyl protecting group was efficiently removed by 'low acidity TfOH' conditions.