(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

Base Information

Chemical Name:(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one
CAS No.:1352995-25-5
Molecular Formula:C₃₆H₆₁IO₄Si
Molecular Weight:712.868
Hs Code.:

(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

Synonyms:(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

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Chemical Property of (3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

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Technology Process of (3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

There total 14 articles about (3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one 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%

: 1352995-23-3
(3Z,5S,6S,7R,9E,11R,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,9,16-trien-8-one

: 1352995-25-5
(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

Guidance literature:: With Stryker's reagent; In toluene; at 0 - 20 ℃; Inert atmosphere;
DOI:10.3762/bjoc.7.161

Reference yield:

: 1352995-07-3
(3S,4R,5S,7R)-8-((tert-butyldimethylsilyl)oxy)-3,5,7-trimethyl-1-(triisopropylsilyl)oct-1-yn-4-ol

: 1352995-25-5
(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 16 h / 20 °C / Inert atmosphere

5.1: pyridine hydrofluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

7.2: Inert atmosphere

8.1: Stryker's reagent / toluene / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; pyridine hydrofluoride; 2-nitrobenzenesulfonyl hydrazide; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; barium(II) hydroxide; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; pentane; 7.1: Horner-Wadsworth-Emmons olefination / 7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.3762/bjoc.7.161

Reference yield:

: 792921-68-7
(3S,4R,5S,7R)-4-(tert-butyldimethylsilyloxy)-7-((tert-butyldimethylsilyloxy)methyl)-3,5-dimethyloct-1-yne

: 1352995-25-5
(3Z,5S,6S,7R,11S,13S,14R,15S,16Z)-14-((tert-butyldimethylsilyl)oxy)-17-iodo-6-((4-methoxybenzyl)oxy)-5,7,11,13,15-pentamethylheptadeca-3,16-dien-8-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: 2-nitrobenzenesulfonyl hydrazide; triethylamine / tetrahydrofuran; isopropyl alcohol / 16 h / 20 °C / Inert atmosphere

3.1: pyridine hydrofluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: Stryker's reagent / toluene / 0 - 20 °C / Inert atmosphere

With pyridine hydrofluoride; 2-nitrobenzenesulfonyl hydrazide; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; barium(II) hydroxide; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene; pentane; 5.1: Horner-Wadsworth-Emmons olefination / 5.2: Horner-Wadsworth-Emmons olefination;
DOI:10.3762/bjoc.7.161