(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

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-dienoic acid methyl ester
• CAS No.: 516457-58-2
• Molecular Formula: C₂₉H₄₅ClO₆Si
• Molecular Weight: 553.211

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-dienoic acid methyl ester

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-dienoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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-dienoic acid methyl ester

There total 16 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-dienoic acid methyl 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:

(2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-ol (118620-86-3,132437-17-3) → (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 (516457-58-2)

Guidance literature:

Multi-step reaction with 16 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

With pyridine; 1H-imidazole; hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; 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 → (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 (516457-58-2)

Guidance literature:

Multi-step reaction with 15 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

With pyridine; 1H-imidazole; hydrogenchloride; N-chloro-succinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; 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

Reference yield:

(4S,5S)-5-(4-Methoxy-benzyloxymethyl)-tetrahydro-furan-2,4-diol → (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 (516457-58-2)

Guidance literature:

Multi-step reaction with 11 steps

1: acetonitrile

2: NaOMe / methanol

3: 42 percent / imidazole

4: 100 percent / LiAlH₄ / tetrahydrofuran

5: pyridine

6: LiBr / dimethylformamide

7: 68 percent / s-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide

8: 45 percent / H₂O; N-chlorosuccinimide / dimethylformamide / 6 h / 50 °C

9: 80 percent / AcOH / tetrahydrofuran; H₂O

10: Dess-Martin periodinane / CH₂Cl₂

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

With pyridine; 1H-imidazole; N-chloro-succinimide; lithium aluminium tetrahydride; 18-crown-6 ether; water; sec.-butyllithium; sodium methylate; potassium hexamethylsilazane; Dess-Martin periodane; acetic acid; lithium bromide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1: Wittig reaction / 10: Dess-Martin oxidation / 11: Still-modified Horner-Emmons reaction;

DOI:10.1021/ol0341804

upstream raw materials:

bis(2,2,2-trifluoroethyl) 1-(methoxycarbonyl)ethylphosphonate

(2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-ol

(2S,3S)-5-Methoxy-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-ol

(4R,5S)-4-Iodomethyl-5-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-[1,3]dioxolane

Downstream raw materials:

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

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

(4Z,7Z)-(S)-3-Acetoxy-8-chloro-10-[(2S,4S,5S)-4-hydroxy-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-4-methyl-deca-4,7-dienoic acid tert-butyl ester

(4Z,7Z)-(S)-10-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-8-chloro-3-hydroxy-4-methyl-deca-4,7-dienoic acid tert-butyl ester

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