methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

Base Information

Chemical Name:methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside
CAS No.:1448225-59-9
Molecular Formula:C₄₉H₄₉NO₁₀
Molecular Weight:811.929
Hs Code.:

Synonyms:methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

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Chemical Property of methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

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Technology Process of methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

There total 6 articles about methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside 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: 88.0%

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

: 329360-22-7
1-O-methyl-3,5-di-O-benzyl-α-D-arabinofuranose

: 1448225-59-9
methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

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:

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

: 1448225-59-9
methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

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

Reference yield:

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

: 1448225-59-9
methyl 2,3-di-O-benzyl-5-O-(2-quinolinecarbonyl)-β-D-arabinofuranosyl-(1→2)-3,5-di-O-benzyl-α-D-arabinofuranoside

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