ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

Base Information

Chemical Name:ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside
CAS No.:1448225-43-1
Molecular Formula:C₂₇H₂₉NO₅S
Molecular Weight:479.597
Hs Code.:

Synonyms:ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

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Chemical Property of ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

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Technology Process of ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

There total 4 articles about ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-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: 93.0%

: 886852-47-7
ethyl 2,3-di-O-benzyl-1-thio-α-D-arabinofuranoside

: 98-98-6
2-Picolinic acid

: 1448225-43-1
ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

Guidance literature:: With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol401755e

Reference yield:

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

: 1448225-43-1
ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol401755e

Reference yield:

: ((2R,3R,4S,5R)-3,4-Bis-benzyloxy-5-ethylsulfanyl-tetrahydro-furan-2-ylmethoxy)-tert-butyl-diphenyl-silane

: 1448225-43-1
ethyl 2,3-di-O-benzyl-5-O-(2-pyridinecarbonyl)-1-thio-α-D-arabinofuranoside

Guidance literature:: Multi-step reaction with 2 steps

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

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

With dmap; tetrabutyl ammonium fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol401755e