methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate

Base Information

• Chemical Name: methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate
• CAS No.: 117300-36-4
• Molecular Formula: C₂₂H₂₉NO₁₄
• Molecular Weight: 531.471

Synonyms:methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate

Chemical Property of methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate

Chemical Property:

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Technology Process of methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate

There total 4 articles about methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate 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: 40.0%

methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate (299179-54-7) + 3-trifluoroacetamidopropyl O-(6-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (432023-49-9) → methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate (117300-36-4) + 3-trifluoroacetamidopropyl O-[methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2->3)-(6-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In acetonitrile; at -20 ℃; for 18h;

DOI:10.1016/S0008-6215(02)00003-4

Reference yield: 18.1%

benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (94926-36-0) + methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chloride)onate (117300-32-0) → C75H83NO24 + methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate (117300-36-4) + benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (117300-33-1) + benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (117300-34-2)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In 1,2-dichloro-ethane; Further byproducts given; 1.) 16 h, 20 deg C; 2.) 70 deg C, 24 h;

DOI:10.1016/0008-6215(88)85082-1

Reference yield: 7.3%

methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chloride)onate (117300-32-0) → benzyl O--(2->4)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (117325-13-0) + methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosyl)onate (117300-36-4) + benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (117300-33-1) + benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (117300-34-2)

Guidance literature:

With benzyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside; 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In 1,2-dichloro-ethane; Further byproducts given; 1.) 16 h, 20 deg C; 2.) 70 deg C, 24 h;

DOI:10.1016/0008-6215(88)85082-1

upstream raw materials:

benzyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside

methyl (5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosyl chloride)onate

methyl (phenyl 5-acetoxyacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-D-galacto-2-nonulopyranoside)onate

3-trifluoroacetamidopropyl O-(6-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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