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Cas Database

1309457-02-0

1309457-02-0

Identification

Synonyms:26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate

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Relevant articles and documentsAll total 1 Articles be found

Stereoselective synthesis of light-activatable perfluorophenylazide- conjugated carbohydrates for glycoarray fabrication and evaluation of structural effects on protein binding by SPR imaging

Deng, Lingquan,Norberg, Oscar,Uppalapati, Suji,Yan, Mingdi,Ramstroem, Olof

experimental part, p. 3188 - 3198 (2011/06/10)

A series of light-activatable perfluorophenylazide (PFPA)-conjugated carbohydrate structures have been synthesized and applied to glycoarray fabrication. The glycoconjugates were structurally varied with respect to anomeric attachment, S-, and O-linked carbohydrates, respectively, as well as linker structure and length. Efficient stereoselective synthetic routes were developed, leading to the formation of the PFPA-conjugated structures in good yields over few steps. The use of glycosyl thiols as donors proved especially efficient and provided the final compounds in up to 70% total yield with high anomeric purities. PFPA-based photochemistry was subsequently used to generate carbohydrate arrays on a polymeric surface, and surface plasmon resonance imaging (SPRi) was applied for evaluation of carbohydrate-protein interactions using the plant lectin Concanavalin A (Con A) as a probe. The results indicate better performance and equal efficiency of S- and O-linked structures with intermediate linker length.

Process route upstream and downstream products

Process route

hexa(ethyleneglycol) ditosylate
42749-27-9

hexa(ethyleneglycol) ditosylate

2-[2-(2-azidoethoxy)ethoxy]ethanol
86520-52-7

2-[2-(2-azidoethoxy)ethoxy]ethanol

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate
1309457-02-0

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 3h; Inert atmosphere;
63%
pentaethylene glycol
2615-15-8

pentaethylene glycol

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate
1309457-02-0

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Inert atmosphere
With dmap; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; mineral oil;
2-[2-(chloroethoxy)ethoxy]ethanol
5197-62-6

2-[2-(chloroethoxy)ethoxy]ethanol

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate
1309457-02-0

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium azide / N,N-dimethyl-formamide / 90 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 20 °C / Inert atmosphere
With sodium azide; sodium hydride; In N,N-dimethyl-formamide; mineral oil;
26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate
1309457-02-0

26-azido-3,6,9,12,15,18,21,24-octaoxahexacosyl 4-methylbenzenesulfonate

C<sub>31</sub>H<sub>48</sub>F<sub>4</sub>N<sub>4</sub>O<sub>14</sub>S
1309457-00-8

C31H48F4N4O14S

Conditions
Conditions Yield
Multi-step reaction with 4 steps
1: sodium iodide / acetone / 1 h / Reflux; Inert atmosphere
2: N,N-dimethyl-formamide / 1 h / 50 °C / Inert atmosphere
3: palladium on carbon; hydrogen / methanol / 1 h / 20 °C
4: N,N-dimethyl-formamide / 2.5 h / 20 °C / Darkness; Inert atmosphere
With palladium on carbon; hydrogen; sodium iodide; In methanol; N,N-dimethyl-formamide; acetone;

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