methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 90124-29-1
• Molecular Formula: C₄₈H₅₉NO₁₈
• Molecular Weight: 937.992
• Mol file: 90124-29-1.mol

Synonyms:

Chemical Property of methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

There total 4 articles about methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 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: 10.4%

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,55094-38-7,68027-27-0,73111-53-2,128184-63-4,138794-99-7,641635-63-4) + N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → Methyl-6-O-(4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-D-glycero-β-D-galakto-2-nonulopyranosidonsaeure-methylester)-2,3,4-tri-O-benzyl-β-D-glucopyranosid (90124-28-0) + methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (90124-29-1)

Guidance literature:

With 2,4,6-trimethyl-pyridine; molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1007/BF00799939

Reference yield:

methyl (1-adamantyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ylopyranosid)onate (956107-32-7) → methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (90124-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane; acetonitrile / 1.5 h / -78 °C / Molecular sieve; Inert atmosphere

2: sodium methylate; methanol / Inert atmosphere

3: pyridine / 0 °C / Inert atmosphere

With pyridine; methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium methylate; In dichloromethane; acetonitrile;

DOI:10.1002/anie.201303781

Reference yield:

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (4356-80-3,34212-64-1,40653-32-5,53008-65-4,55094-38-7,68027-27-0,73111-53-2,128184-63-4,138794-99-7,641635-63-4) → methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside (90124-29-1)

Guidance literature:

Multi-step reaction with 3 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane; acetonitrile / 1.5 h / -78 °C / Molecular sieve; Inert atmosphere

2: sodium methylate; methanol / Inert atmosphere

3: pyridine / 0 °C / Inert atmosphere

With pyridine; methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium methylate; In dichloromethane; acetonitrile;

DOI:10.1002/anie.201303781

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside

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

methyl (1-adamantyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ylopyranosid)onate