methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside

Base Information

• Chemical Name: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside
• CAS No.: 116113-13-4
• Molecular Formula: C₃₂H₄₇NO₁₈
• Molecular Weight: 733.721

Synonyms:

Chemical Property of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside

There total 3 articles about methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 3.0%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (116113-13-4,89733-58-4) + methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2)

Guidance literature:

With silver (II) carbonate; In dichloromethane; Title compound not separated from byproducts; -20 deg C 15 hour, room temp. 50 hour.;

DOI:10.1016/0008-6215(84)85141-1

Reference yield:

methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate (1071226-27-1) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (116113-13-4,89733-58-4) + methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside (89733-58-4,116113-13-4)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; at -40 ℃; for 1h; Overall yield = 83 %; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2012.08.007

Reference yield:

methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate (1071226-27-1) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → O--(2->6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose (116113-13-4,89733-58-4) + methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate (73960-72-2) + methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonate-(2 → 6)-1,2;3,4-di-O-isopropylidene-α-D-galactopyranoside (89733-58-4,116113-13-4)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; at -40 ℃; for 1h; Overall yield = 83 %; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2012.08.007

upstream raw materials:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate

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