213327-09-4

Basic information

• Product Name: N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-octyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS NO: 213327-09-4
• Molecular Weight: 675.817
• Mol File: 213327-09-4.mol

Chemical Properties

• CAS DataBase Reference: N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-octyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-octyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide(213327-09-4)
• EPA Substance Registry System: N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-2-octyloxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide(213327-09-4)

Safety Data

• Hazardous Substances Data: 213327-09-4(Hazardous Substances Data)

Upstream product

• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 196876-45-6 octyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 108-24-7 acetic anhydride 
• 880145-28-8 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester 

Downstream Products

• 213327-10-7 N-[(2R,3R,4R,5S,6R)-4-Benzyloxy-5-((2S,3R,4S,5R,6R)-3-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-tetrahydro-pyran-2-yloxy)-6-benzyloxymethyl-2-octyloxy-tetrahydro-pyran-3-yl]-acetamide 
• 213327-16-3 C₇₈H₈₇NO₂₀ 
• 213327-15-2 C₇₁H₈₇NO₂₁ 
• 178977-64-5 octyl (β-D-galactopyranosyl)-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of oligosaccharides designed to form micelles, corresponding to structures found in ovarian cyst fluid

The syntheses of α-D-GlcpNAc-(1 →4)-β-D-Galp-(1→4)-β-D-GlcNAc-(1→O)-(CH2)15CH3 (1) and fragments thereof, corresponding to structures found in human ovarian cyst fluid, are described. Silver triflate promoted coupling of 3.4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl bromide (12) and galactose acceptor (11) gave a disaccharide donor (13), which was readily transformed into the corresponding bromoderivative 18. For the synthesis of disaccharide β-D-Galp-(1 →4)-D-GlcNAc, several differently protected glucosamine acceptors were prepared. It was found that cetyl alcohol needed to be introduced after the formation of the β-galactoside bond. Glycosylation of pent-4-enyl 3,6-di-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D-glucopyranoside (30) with (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1 →4)-2,3,6-tri-O-benzoyl-α-D-galactopyranosyl bromide (18) by use of silver triflate as promoter gave the desired trisaccharide 31. Finally 31 was transformed via coupling to the long alkyl chain aglycon and deprotection into the title compound 1.

Efficient synthesis of 3'-glycosylated LacNac-based oligosaccharides

LacNAc-based oligosaccharides, including sialyl-(2→3)-LacNAc, dimeric sialyl-(2→3)-LacNAc, trimeric sialyl-(2→3)-LacNAc, β-glucuronyl-(1→3)- LacNAc, and 3-sulfo-β-glucuronyl-(1→3)-LacNAc, were synthesized efficiently from a single protected LacNAc derivative having both OH-3' and 4' unprotected.