N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside

Base Information

• Chemical Name: N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside
• CAS No.: 1269467-10-8
• Molecular Formula: C₆₆H₆₉NO₁₄
• Molecular Weight: 1100.27

Synonyms:N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside

Chemical Property of N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside

There total 14 articles about N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside 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: 91.0%

N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside (1269467-08-4) → N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside (1269467-10-8)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/ol200192d

Reference yield: 32.0%

benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester (920958-49-2) + 4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside (1269466-61-6) + p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside (1269466-90-1) → N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside (1269467-10-8)

Guidance literature:

4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside; p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside; With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -78 ℃; Inert atmosphere;

With trifluorormethanesulfonic acid; In dichloromethane; at -78 - -5 ℃; for 3h; Inert atmosphere;

benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester; With trifluorormethanesulfonic acid; In dichloromethane; 2,2'-iminobis[ethanol]; at -55 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol200192d

Reference yield:

benzoic acid anhydride (93-97-0) → N-(benzyl)benzyloxycarbonyl-5-aminopentyl 2-O-benzoyl-4-O-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-3-O-benzyl-β-D-xylopyranoside (1269467-10-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ytterbium(III) triflate / 1,4-dioxane / 14 h / 20 °C / Inert atmosphere

2.1: N-iodo-succinimide / dichloromethane; acetonitrile / 0.17 h / -40 °C / Inert atmosphere

2.2: 2 h / -40 °C / Inert atmosphere

3.1: N-iodo-succinimide / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 - -20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate / acetonitrile / 0.5 h / 0 °C

With N-iodo-succinimide; boron trifluoride diethyl etherate; ytterbium(III) triflate; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1021/ol200192d

upstream raw materials:

benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester

4-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-xylopyranoside

p-methylphenyl 2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-1-thio-β-D-galactoside

4-methylphenyl 1-thio-β-D-xylopyranoside

Downstream raw materials:

N-(benzyl)benzyloxycarbonyl-5-aminopentyl (2-O-benzoyl-4,6-di-O-benzyl-3-O-tert-butyldimethylsilyl-β-D-galactopyranosyl)-(1->3)-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-O-benzoyl-3-O-benzyl-β-D-xylopyranoside

N-(benzyl)benzyloxycarbonyl-5-aminopentyl (2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->3)-(2-O-benzoyl-4,6-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-O-benzoyl-3-O-benzyl-β-D-xylopyranoside

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