(12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester

Base Information

• Chemical Name: (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester
• CAS No.: 214405-84-2
• Molecular Formula: C₅₅H₁₀₂O₁₃SSi
• Molecular Weight: 1031.56

Synonyms:(12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester

Chemical Property of (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester

Chemical Property:

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Technology Process of (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester

There total 16 articles about (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + ethyl (12R,15S,16S,19R,20R,23R,24S)-12-[(tert-butyldimethylsilyl)oxy]-15-hydroxy-16,19,24-tri(methoxymethoxy)-20,23-oxidotetratriacontanoate (214405-83-1) → (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester (214405-84-2)

Guidance literature:

With pyridine; at 20 ℃; for 12h;

DOI:10.1021/jo981103r

Reference yield:

(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal (204572-66-7) → (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester (214405-84-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 88 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

2: 96 percent / pyridine / 12 h

3: 88 percent / TBAF / tetrahydrofuran / 12 h / 50 °C

4: 92 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / 20 °C

5: 97 percent / H₂ / Pd-C / ethanol / 12 h

6: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7: 90 percent / InCl₃ / ethyl acetate / 2 h / -78 - 20 °C

8: 90 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / 20 °C

9: 95 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 4 h

10: 98 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

11: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

12: 63 percent / (1S,2S)-1,2-bis(trifluoromethanesulfonamido)cyclohexane / Ti(O-i-Pr)4 / toluene / 12 h / -20 °C

13: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

14: 86 percent / H₂ / Pd-C / ethyl acetate; ethanol / 12 h

15: 95 percent / pyridine / 12 h / 20 °C

With pyridine; 1H-imidazole; indium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide; titanium(IV) isopropylate; palladium on activated charcoal; rhodium on alumina; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Addition / 2: Tosylation / 3: Cyclization / 4: Etherification / 5: Catalytic hydrogenation / 6: Dess-Martin oxidation / 7: Addition / 8: Etherification / 9: Catalytic hydrogenation / 10: desilylation / 11: Dess-Martin oxidation / 12: Addition / 13: silylation / 14: Hydrogenolysis / 15: Tosylation;

DOI:10.1021/jo981103r

Reference yield:

Tributyl-[(R)-1-((Z)-2-methoxymethoxy-vinyl)-nonyl]-stannane → (12R,15R,16S,19R)-12-(tert-Butyl-dimethyl-silanyloxy)-16,19-bis-methoxymethoxy-19-[(2R,5R)-5-((S)-1-methoxymethoxy-undecyl)-tetrahydro-furan-2-yl]-15-(toluene-4-sulfonyloxy)-nonadecanoic acid ethyl ester (214405-84-2)

Guidance literature:

Multi-step reaction with 15 steps

1: 88 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -78 °C

2: 96 percent / pyridine / 12 h

3: 88 percent / TBAF / tetrahydrofuran / 12 h / 50 °C

4: 92 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / 20 °C

5: 97 percent / H₂ / Pd-C / ethanol / 12 h

6: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7: 90 percent / InCl₃ / ethyl acetate / 2 h / -78 - 20 °C

8: 90 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / 20 °C

9: 95 percent / H₂ / Rh-Al₂O₃ / ethyl acetate / 4 h

10: 98 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

11: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

12: 63 percent / (1S,2S)-1,2-bis(trifluoromethanesulfonamido)cyclohexane / Ti(O-i-Pr)4 / toluene / 12 h / -20 °C

13: 95 percent / imidazole / dimethylformamide / 12 h / 20 °C

14: 86 percent / H₂ / Pd-C / ethyl acetate; ethanol / 12 h

15: 95 percent / pyridine / 12 h / 20 °C

With pyridine; 1H-imidazole; indium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide; titanium(IV) isopropylate; palladium on activated charcoal; rhodium on alumina; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 1: Addition / 2: Tosylation / 3: Cyclization / 4: Etherification / 5: Catalytic hydrogenation / 6: Dess-Martin oxidation / 7: Addition / 8: Etherification / 9: Catalytic hydrogenation / 10: desilylation / 11: Dess-Martin oxidation / 12: Addition / 13: silylation / 14: Hydrogenolysis / 15: Tosylation;

DOI:10.1021/jo981103r

upstream raw materials:

p-toluenesulfonyl chloride

ethyl (12R,15S,16S,19R,20R,23R,24S)-12-[(tert-butyldimethylsilyl)oxy]-15-hydroxy-16,19,24-tri(methoxymethoxy)-20,23-oxidotetratriacontanoate

(4R,5R)-8-Benzyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-octanal

(4R,5R,8R,9S)-4,9-di(methoxymethoxy)-5,8-oxidononadecanal

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