10-Tetradecenoic acid, 12-hydroxy-9-oxo-13-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (10E,12S,13S)-

Base Information

Chemical Name:10-Tetradecenoic acid, 12-hydroxy-9-oxo-13-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (10E,12S,13S)-
CAS No.:676335-59-4
Molecular Formula:C₂₃H₃₃NO₆
Molecular Weight:419.518
Hs Code.:

Synonyms:

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Chemical Property of 10-Tetradecenoic acid, 12-hydroxy-9-oxo-13-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (10E,12S,13S)-

Chemical Property:

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Technology Process of 10-Tetradecenoic acid, 12-hydroxy-9-oxo-13-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (10E,12S,13S)-

There total 11 articles about 10-Tetradecenoic acid, 12-hydroxy-9-oxo-13-[[(phenylmethoxy)carbonyl]amino]-, methyl ester, (10E,12S,13S)- 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:

: 14436-32-9
dec-9-enoic acid

: 676335-59-4
(E)-(12S,13S)-13-Benzyloxycarbonylamino-12-hydroxy-9-oxo-tetradec-10-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / H₂SO₄

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 72 percent / Zn; HOAc

3.1: 78 percent / CrCl₂; NiBr₂ / dimethylformamide

4.1: 93 percent / DMP / CH₂Cl₂

5.1: (IHMes)Cl₂Ru(2-iPrOC₆H₄CH=) / toluene / 80 °C

6.1: TBAF / tetrahydrofuran

With chromium dichloride; phthalic acid dimethyl ester; sulfuric acid; tetrabutyl ammonium fluoride; ozone; nickel dibromide; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Nozaki-Hiyama-Kishi reaction / 4.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2003.12.010

Reference yield:

: 25601-41-6
methyl 9-decenoate

: 676335-59-4
(E)-(12S,13S)-13-Benzyloxycarbonylamino-12-hydroxy-9-oxo-tetradec-10-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 72 percent / Zn; HOAc

2.1: 78 percent / CrCl₂; NiBr₂ / dimethylformamide

3.1: 93 percent / DMP / CH₂Cl₂

4.1: (IHMes)Cl₂Ru(2-iPrOC₆H₄CH=) / toluene / 80 °C

5.1: TBAF / tetrahydrofuran

With chromium dichloride; phthalic acid dimethyl ester; tetrabutyl ammonium fluoride; ozone; nickel dibromide; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: Nozaki-Hiyama-Kishi reaction / 3.1: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2003.12.010

Reference yield:

: 1931-63-1
methyl ester of azelaic acid aldehyde

: 676335-59-4
(E)-(12S,13S)-13-Benzyloxycarbonylamino-12-hydroxy-9-oxo-tetradec-10-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / CrCl₂; NiBr₂ / dimethylformamide

2: 93 percent / DMP / CH₂Cl₂

3: (IHMes)Cl₂Ru(2-iPrOC₆H₄CH=) / toluene / 80 °C

4: TBAF / tetrahydrofuran

With chromium dichloride; phthalic acid dimethyl ester; tetrabutyl ammonium fluoride; nickel dibromide; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Nozaki-Hiyama-Kishi reaction / 2: Dess-Martin oxidation;
DOI:10.1016/j.tetlet.2003.12.010