ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

Base Information

Chemical Name:ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside
CAS No.:1415590-63-4
Molecular Formula:C₂₈H₃₁NO₅S
Molecular Weight:493.624
Hs Code.:

Synonyms:ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

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Chemical Property of ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

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Technology Process of ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

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

: 98-98-6
2-Picolinic acid

: 1415590-67-8
ethyl 2,4-di-O-benzyl-1-thio-β-L-rhamnopyranoside

: 1415590-63-4
ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1002/ejoc.201901186

Reference yield:

: 152488-30-7
ethyl 2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside

: 1415590-63-4
ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

5.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; tetrabutyl ammonium fluoride; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja307355n

Reference yield:

: 1415590-64-5
ethyl 4-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-1-thio-β-L-rhamnopyranoside

: 1415590-63-4
ethyl 2,4-di-O-benzyl-3-O-(2-pyridinecarbonyl)-1-thio-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane; water / 0.5 h / 20 °C

2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 20 °C

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C

4: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

With dmap; tetrabutyl ammonium fluoride; sodium hydride; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/ja307355n