(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

Base Information

Chemical Name:(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol
CAS No.:516457-60-6
Molecular Formula:C₂₈H₄₅ClO₅Si
Molecular Weight:525.201
Hs Code.:

Synonyms:(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

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Chemical Property of (2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

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Technology Process of (2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

There total 17 articles about (2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol 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: 100.0%

: 516457-58-2
(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dienoic acid methyl ester

: 516457-60-6
(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene;
DOI:10.1021/ol0341804

Reference yield:

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

: 516457-60-6
(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

Guidance literature:: Multi-step reaction with 17 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

With pyridine; 1H-imidazole; hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; calcium carbonate; sodium iodide; lithium bromide; In tetrahydrofuran; 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

: 516457-60-6
(2Z,5Z)-8-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-6-chloro-2-methyl-octa-2,5-dien-1-ol

Guidance literature:: Multi-step reaction with 16 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

With pyridine; 1H-imidazole; hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; calcium carbonate; sodium iodide; lithium bromide; In tetrahydrofuran; 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