Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

Base Information

Chemical Name:Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester
CAS No.:516457-80-0
Molecular Formula:C₂₄H₃₂BrClO₆
Molecular Weight:531.871
Hs Code.:

Synonyms:Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

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Chemical Property of Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

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Technology Process of Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

There total 21 articles about Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl 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:

: 516457-79-7
Bromo-acetic acid (2S,3S,5S)-5-{(3Z,6Z)-3-chloro-8-[(4-methoxy-phenyl)-diphenyl-methoxy]-7-methyl-octa-3,6-dienyl}-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

: 516457-80-0
Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; water;
DOI:10.1021/ol0341804

Reference yield:

: 118620-86-3,132437-17-3
(2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-ol

: 516457-80-0
Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 21 steps

1: pyridine

2: NaI; CaCO₃ / acetone

3: 87 percent / n-BuLi / tetrahydrofuran; hexane

4: 58 percent / conc. HCl

5: 99 percent / 1 M HCl / H₂O; tetrahydrofuran

6: acetonitrile

7: NaOMe / methanol

8: 42 percent / imidazole

9: 100 percent / LiAlH₄ / tetrahydrofuran

10: pyridine

11: LiBr / dimethylformamide

12: 68 percent / s-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide

13: 45 percent / H₂O; N-chlorosuccinimide / dimethylformamide / 6 h / 50 °C

14: 80 percent / AcOH / tetrahydrofuran; H₂O

15: Dess-Martin periodinane / CH₂Cl₂

16: KHMDS; 18-crown-6 / tetrahydrofuran; toluene

17: 100 percent / DIBAL / toluene

18: 100 percent / pyridine

19: 99 percent / TBAF / tetrahydrofuran

20: pyridine / CH₂Cl₂

21: AcOH / tetrahydrofuran; H₂O

With pyridine; 1H-imidazole; hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; calcium carbonate; sodium iodide; lithium bromide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 6: Wittig reaction / 15: Dess-Martin oxidation / 16: Still-modified Horner-Emmons reaction;
DOI:10.1021/ol0341804

Reference yield:

: Toluene-4-sulfonic acid (4S,5S)-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 516457-80-0
Bromo-acetic acid (2S,3S,5S)-5-((3Z,6Z)-3-chloro-8-hydroxy-7-methyl-octa-3,6-dienyl)-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

Guidance literature:: Multi-step reaction with 20 steps

1: NaI; CaCO₃ / acetone

2: 87 percent / n-BuLi / tetrahydrofuran; hexane

3: 58 percent / conc. HCl

4: 99 percent / 1 M HCl / H₂O; tetrahydrofuran

5: acetonitrile

6: NaOMe / methanol

7: 42 percent / imidazole

8: 100 percent / LiAlH₄ / tetrahydrofuran

9: pyridine

10: LiBr / dimethylformamide

11: 68 percent / s-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide

12: 45 percent / H₂O; N-chlorosuccinimide / dimethylformamide / 6 h / 50 °C

13: 80 percent / AcOH / tetrahydrofuran; H₂O

14: Dess-Martin periodinane / CH₂Cl₂

15: KHMDS; 18-crown-6 / tetrahydrofuran; toluene

16: 100 percent / DIBAL / toluene

17: 100 percent / pyridine

18: 99 percent / TBAF / tetrahydrofuran

19: pyridine / CH₂Cl₂

20: AcOH / tetrahydrofuran; H₂O

With pyridine; 1H-imidazole; hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; tetrabutyl ammonium fluoride; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; calcium carbonate; sodium iodide; lithium bromide; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5: Wittig reaction / 14: Dess-Martin oxidation / 15: Still-modified Horner-Emmons reaction;
DOI:10.1021/ol0341804