3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

Base Information

Chemical Name:3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside
CAS No.:1448225-70-4
Molecular Formula:C₅₉H₅₄N₄O₁₄
Molecular Weight:1043.1
Hs Code.:

Synonyms:3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

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Chemical Property of 3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

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Technology Process of 3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

There total 6 articles about 3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside 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%

: 1448225-46-4
ethyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-1-thio-α-D-arabinofuranoside

: 1439439-43-6
3-azidopropyl 2,3,4-tri-O-benzoyl-α-D-mannopyranoside

: 1448225-70-4
3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

Guidance literature:: With N-iodo-succinimide; trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at -30 - 0 ℃; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1021/ol401755e

Reference yield:

: 118924-06-4
ethyl 1-thio-α-D-arabinofuranoside

: 1448225-70-4
3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: N-iodo-succinimide; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / -30 - 0 °C / Inert atmosphere; Molecular sieve

With 1H-imidazole; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/ol401755e

Reference yield:

: 1448225-42-0
ethyl 5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside

: 1448225-70-4
3-azidopropyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→6)-2,3,4-tri-O-benzoyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 1 h / 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dmap / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.1: N-iodo-succinimide; trifluorormethanesulfonic acid / 1,2-dichloro-ethane / -30 - 0 °C / Inert atmosphere; Molecular sieve

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/ol401755e