(2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester
• CAS No.: 126168-67-0
• Molecular Formula: C₄₂H₅₁NO₂₀
• Molecular Weight: 889.862

Synonyms:

Chemical Property of (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

There total 4 articles about (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester 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:

1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9) → (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (126168-67-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂, acetic acid / 5percent Pd/C / 3 h / 760 Torr

2: 82 percent / p-toluenesulfonic acid / acetonitrile / 0.5 h

3: silver trifluoromethanesulfonate, 2,6-di-tert-butylpyridine / tetrahydrofuran / 5 h / -55 - 0 °C

With 2,6-di-tert-butyl-pyridine; hydrogen; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; acetic acid; palladium on activated charcoal; In tetrahydrofuran; acetonitrile;

DOI:10.1016/0008-6215(93)84162-Y

Reference yield:

benzyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulpyranosid)onate (113757-77-0) + 1-O-acetyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranose (126151-75-5) → (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (126168-67-0)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate; In tetrahydrofuran; at -55 - 0 ℃; for 5h;

DOI:10.1016/0008-6215(93)84162-Y

Reference yield:

benzyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulpyranosylonate (194856-21-8) → (2S,4S,5R,6R)-4-Acetoxy-2-[(4aR,6S,7R,8R,8aS)-6-acetoxy-7-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (126168-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: acetyl chloride, conc. HCl / CH₂Cl₂ / 22 °C

2: silver trifluoromethanesulfonate, 2,6-di-tert-butylpyridine / tetrahydrofuran / 5 h / -55 - 0 °C

With hydrogenchloride; 2,6-di-tert-butyl-pyridine; silver trifluoromethanesulfonate; acetyl chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0008-6215(93)84162-Y

upstream raw materials:

benzyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

1-O-acetyl-4,6-O-p-methoxybenzylidene-β-D-galactopyranose

1-O-acetyl-2,3,4,6-tetra-O-benzyl-β-D-galactopyranoside

benzyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulpyranosylonate

Downstream raw materials:

O-(benzyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2<*>3)-1,2,4,6-tetra-O-acetyl-β-D-galactopyranose

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