(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

Base Information

Chemical Name:(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one
CAS No.:888488-17-3
Molecular Formula:C₄₇H₉₂O₇Si₃
Molecular Weight:853.5
Hs Code.:

(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

Synonyms:(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

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Chemical Property of (3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

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Technology Process of (3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

There total 14 articles about (3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-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: 78.0%

: 888488-09-3
(2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal

: 888488-08-2
(4R,5R,6R,7R)-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one

: (3R,4R,5R,6R,8R,9R,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

: 888488-17-3
(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

Guidance literature:: (4R,5R,6R,7R)-7-tert-butyldimethylsilyloxy-5-triethylsilyloxy-4,6,8-trimethylnon-3-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -50 ℃; for 1h;

(2S,3S,4S,5S)-3-(tert-butyldimethylsilyloxy)-5-(p-methoxybenzyloxy)-2,4-dimethylheptanal; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1021/ol060347s

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 888488-17-3
(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

2.1: LiBH₄ / tetrahydrofuran / 24 h / -78 - 20 °C

2.2: 462 mg / NaIO₄ / methanol; H₂O / 0.17 h / 20 °C

3.1: dicyclohexylboron chloride; Me₂NEt / diethyl ether / -78 - 0 °C

3.2: 77 percent / diethyl ether / 16 h / -78 - -23 °C

4.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

5.1: 94 percent / SmI₂ / tetrahydrofuran; methanol / 0 °C

6.1: LiHMDS / tetrahydrofuran / 1 h / -78 - -50 °C

6.2: 78 percent / tetrahydrofuran / 2 h / -78 °C

With 2,6-dimethylpyridine; lithium borohydride; samarium diiodide; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.2: aldol reaction / 6.2: aldol reaction;
DOI:10.1021/ol060347s

Reference yield:

: 888488-12-8
(4R,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one

: 888488-17-3
(3R,4R,5R,6R,8R,9S,10R,11R,12S,13S)-3,11-bis-[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-9-hydroxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxybenzyloxy]pentadec-7-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / NaBH₄ / ethanol / 5 h / 0 - 20 °C

2.1: 84 percent / trifluoromethanesulfonic acid / diethyl ether / 0 - 20 °C

3.1: 87 percent / H₂ / W-2 Raney nickel / ethanol / 6 h / 20 °C

4.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: LiHMDS / tetrahydrofuran / 1 h / -78 - -50 °C

5.2: 78 percent / tetrahydrofuran / 2 h / -78 °C

With sodium tetrahydroborate; trifluorormethanesulfonic acid; hydrogen; Dess-Martin periodane; lithium hexamethyldisilazane; W-2 Raney nickel; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 4.1: Dess-Martin oxidation / 5.2: aldol reaction;
DOI:10.1021/ol060347s