(E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

Base Information

Chemical Name:(E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester
CAS No.:186021-16-9
Molecular Formula:C₄₄H₅₅NO₁₂
Molecular Weight:789.92
Hs Code.:

Synonyms:(E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

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Chemical Property of (E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

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Technology Process of (E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

There total 5 articles about (E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester 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: 83.0%

: 71989-35-0,138797-71-4
Fmoc-Thr(tBu)-OH

: 186021-07-8
(E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

: 186021-16-9
(E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

Guidance literature:: With tetrabutylammomium bromide; sodium hydrogencarbonate; In dichloromethane;
DOI:10.1021/jo960743w

Reference yield:

: 166668-33-3
(E)-17-bromo-4,7,10,13-tetraoxa-15-heptadecenoic acid tert-butyl ester

: 186021-16-9
(E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 82 percent / TFA / 0.75 h

2: KF / dimethylformamide / 0.75 h

3: 83 percent / Bu₄NBr, aq. NaHCO₃ / CH₂Cl₂

With potassium fluoride; tetrabutylammomium bromide; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo960743w

Reference yield:

: 186020-66-6,892154-71-1
3-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-propionic acid tert-butyl ester

: 186021-16-9
(E)-17-[N-(9-fluorenylmethoxycarbonyl)-O-tert-butyl-L-threonyloxy]-4,7,10,13-tetraoxa-15-heptadecenoic acid phenacyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 45 percent / NaOH, Bu₄NHSO₄ / H₂O; CH₂Cl₂ / 0.75 h

2: 82 percent / TFA / 0.75 h

3: KF / dimethylformamide / 0.75 h

4: 83 percent / Bu₄NBr, aq. NaHCO₃ / CH₂Cl₂

With potassium fluoride; sodium hydroxide; tetrabutylammomium bromide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo960743w