(5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one

Base Information

• Chemical Name: (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one
• CAS No.: 1356108-63-8
• Molecular Formula: C₄₆H₈₄O₇Si₂
• Molecular Weight: 805.34

Synonyms:

Chemical Property of (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one

Chemical Property:

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Technology Process of (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one

There total 1 articles about (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-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: 12.0%

C19H36O2Si (1268687-73-5) + (5S,6S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one (1268687-74-6) → (5S,6S,7S,10R,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5 trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disilaheptadecan-9-one (1356108-66-1) + (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one (1356108-63-8)

Guidance literature:

(5S,6S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one; With titanium tetrachloride; triethylamine; In dichloromethane; at -78 ℃; for 1h; Inert atmosphere;

C₁₉H₃₆O₂Si; In tetrahydrofuran; at -78 - 0 ℃; for 3.5h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/ejoc.201101129

Reference yield:

carbon disulfide (75-15-0,12122-00-8) + (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one (1356108-63-8) + methyl iodide (74-88-4) → C48H86O7S2Si2

Guidance literature:

carbon disulfide; (5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 - 0 ℃; for 6h;

DOI:10.1002/ejoc.201101129

Reference yield:

(5S,6S,7S,10S,11R,12S,13S)-11-hydroxy-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethylhexa-1,4-dienyl]-4,14-dioxa-3,15-disila-heptadecan-9-one (1356108-63-8) → (5S,6S,7S,10S,12S,13S)-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethyl-hexa-1,4-dienyl]-4,14-dioxa-3,15-disilaheptadecan-9-one (1268688-01-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: 6 h / -78 - 0 °C

2.1: triethyl borane; tri-n-butyl-tin hydride / hexane; toluene / 1 h / 20 °C / Inert atmosphere

With triethyl borane; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; toluene; 2.1: Barton-McCombie deoxygenation;

DOI:10.1002/ejoc.201101129

upstream raw materials:

C₁₉H₃₆O₂Si

(5S,6S,7S)-7-[(tert-butyldimethylsilyl)oxy]-5-methoxy-9-[(4-methoxybenzyl)oxy]-4,4,6-trimethylnonan-3-one

Downstream raw materials:

(5S,6S,7S,10S,12S,13S)-7-methoxy-5-{2-[(4-methoxybenzyl)oxy]ethyl}-2,2,3,3,6,8,8,10,12,15,15,16,16-tridecamethyl-13-[(1E,3S)-1,3,5-trimethyl-hexa-1,4-dienyl]-4,14-dioxa-3,15-disilaheptadecan-9-one

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