E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

Base Information

Chemical Name:E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid
CAS No.:639808-08-5
Molecular Formula:C₃₆H₅₁N₃O₅Si
Molecular Weight:633.904
Hs Code.:

Synonyms:E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

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Chemical Property of E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

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Technology Process of E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

There total 9 articles about E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid 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: 84.0%

: 7530-96-3
(11-carboxyundecyl)triphenylphosphonium bromide

: (2R,3R,4R,5R)-3-Allyloxy-5-azidomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

: 639808-08-5
E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

Guidance literature:: (11-carboxyundecyl)triphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 1h;

(2R,3R,4R,5R)-3-Allyloxy-5-azidomethyl-4-(tert-butyl-diphenyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde; In tetrahydrofuran; toluene; at -78 - 20 ℃;
DOI:10.1021/jo0349429

Reference yield:

: 106248-72-0
2,5-Anhydro-1,3-O-isopropyliden-6-O-(p-tosyl)-D-glucitol

: 639808-08-5
E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium azide; tetra-n-butylammonium iodide / dimethylformamide / 16 h / 80 °C

2.1: 33 g / imidazole / dimethylformamide / 20 °C

3.1: trifluoroacetic acid / methanol; CH₂Cl₂ / 3 h

4.1: pyridine / 16 h

5.1: 7.8 g / potassium hexamethyldisilazane (KHMDS) / dimethylformamide; toluene / 0 - 20 °C

6.1: 99 percent / triisopropylsilane (TiPSH); TFA / CH₂Cl₂ / 0.5 h

7.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

8.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

8.2: 84 percent / tetrahydrofuran; toluene / -78 - 20 °C

With pyridine; 1H-imidazole; sodium azide; potassium hexamethyldisilazane; chlorotriisopropylsilane; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 8.2: Wittig reaction;
DOI:10.1021/jo0349429

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 639808-08-5
E/Z-12-[(2S,3R,4S,5R)-3-allyloxy-5-azidomethyl-4-tert-butyldiphenylsilanyloxytetrahydrofuran-2-yl]dodec-11-enoic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: 33 g / imidazole / dimethylformamide / 20 °C

2.1: trifluoroacetic acid / methanol; CH₂Cl₂ / 3 h

3.1: pyridine / 16 h

4.1: 7.8 g / potassium hexamethyldisilazane (KHMDS) / dimethylformamide; toluene / 0 - 20 °C

5.1: 99 percent / triisopropylsilane (TiPSH); TFA / CH₂Cl₂ / 0.5 h

6.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

7.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 °C

7.2: 84 percent / tetrahydrofuran; toluene / -78 - 20 °C

With pyridine; 1H-imidazole; potassium hexamethyldisilazane; chlorotriisopropylsilane; potassium hexamethylsilazane; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 7.2: Wittig reaction;
DOI:10.1021/jo0349429