N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside
CAS No.:1431139-47-7
Molecular Formula:C₅₃H₆₃NO₁₀
Molecular Weight:874.084
Hs Code.:

Synonyms:N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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Technology Process of N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

There total 4 articles about N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside 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: 92.0%

: 920958-49-2
benzyl-(5-hydroxy-pentyl)-carbamic acid benzyl ester

: 1431139-39-7
p-tolyl 2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

: 1431139-47-7
N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/ol4008475

Reference yield:

: 1225554-05-1
2,2-dimethyl-4-(4-methoxyphenoxy)butanoic acid

: 1431139-47-7
N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl dichloride / dichloromethane / Reflux; Inert atmosphere

2.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C

With 1H-imidazole; N-iodo-succinimide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; In tetrahydrofuran; dichloromethane; mineral oil;
DOI:10.1021/ol4008475

Reference yield:

: 1431139-33-1
ethyl 4-(4-methoxyphenoxy)-2,2-dimethylbutanoate

: 1431139-47-7
N-benzyl-N-benzyloxycarbonyl-5-aminopentanyl-2-O-(2,2-dimethyl-4-(4-methoxyphenoxy)butanoyl)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hydroxide / ethanol; water / 3 h / Reflux

2.1: oxalyl dichloride / dichloromethane / Reflux; Inert atmosphere

3.1: 1H-imidazole; sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C

With 1H-imidazole; N-iodo-succinimide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; lithium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; mineral oil;
DOI:10.1021/ol4008475