(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

Base Information

Chemical Name:(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid
CAS No.:479673-46-6
Molecular Formula:C₄₆H₆₈O₇
Molecular Weight:733.042
Hs Code.:

Synonyms:(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

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Chemical Property of (10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

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Technology Process of (10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

There total 22 articles about (10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic 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: 57.0%

: 479673-27-3
(10Z,15Z,23Z)-(12S,13S,14S,19R,20S,21S,22S)-21-(tert-Butyl-dimethyl-silanyloxy)-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

: 479673-46-6
(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

Guidance literature:: With tetrabutyl ammonium fluoride;
DOI:10.1021/ol026942l

Reference yield:

: 154919-93-4
(S)-4-Benzyl-3-[(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hexanoyl]-oxazolidin-2-one

: 479673-46-6
(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

Guidance literature:: Multi-step reaction with 16 steps

1.1: LiBH₄

1.2: PPTS

2.1: 92 percent / DIBAL

3.1: Dess-Martin periodinane

4.1: 85 percent / LDA

5.1: 88 percent / 2,6-lutidine

6.1: 79 percent / DIBAL

7.1: Dess-Martin periodinane

8.1: CrCl₂

8.2: NaH

9.1: 88 percent / HF*pyridine / pyridine

10.1: I₂; PPh₃; imidazole

11.1: NaHMDS

12.1: 78 percent / HF*pyridine / pyridine

13.1: Dess-Martin periodinane

14.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄

15.1: 57 percent / TBAF

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; iodine; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; lithium diisopropyl amide; In pyridine; 3.1: Dess-Martin oxidation / 7.1: Dess-Martin oxidation / 8.1: Peterson olefination / 8.2: Peterson olefination / 12.1: Wittig reaction / 14.1: Dess-Martin oxidation;
DOI:10.1021/ol026942l

Reference yield:

: 112-47-0
1,10-Decanediol

: 479673-46-6
(10Z,15Z,23Z)-(12S,13S,14S,19R,20R,21S,22S)-21-Hydroxy-13,19-bis-(4-methoxy-benzyloxy)-12,14,20,22-tetramethyl-hexacosa-10,15,23,25-tetraenoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 42 percent / NaH

2: 80 percent / Dess-Martin periodinane

3: 75 percent / NaHMDS

4: 70 percent / DIBAL

5: Dess-Martin periodinane

6: NaHMDS

7: 78 percent / HF*pyridine / pyridine

8: Dess-Martin periodinane

9: NaClO₂; 2-methyl-2-butene; NaH₂PO₄

10: 57 percent / TBAF

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; In pyridine; 2: Dess-Martin oxidation / 3: Wittig reaction / 5: Dess-Martin oxidation / 6: Wittig reaction / 8: Dess-Martin oxidation;
DOI:10.1021/ol026942l