(3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione

Base Information

• Chemical Name: (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione
• CAS No.: 888488-07-1
• Molecular Formula: C₄₇H₉₀O₇Si₃
• Molecular Weight: 851.484
• Mol file: 888488-07-1.mol

Synonyms:(3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione

Chemical Property of (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione

There total 15 articles about (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione 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: 88.0%

(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 (888488-17-3) → (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione (888488-07-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ol060347s

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione (888488-07-1)

Guidance literature:

Multi-step reaction with 7 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

7.1: 88 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 0 °C

With 2,6-dimethylpyridine; lithium borohydride; samarium diiodide; oxalyl dichloride; N,N-dimethyl-ethanamine; dicyclohexylboron chloride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3.2: aldol reaction / 6.2: aldol reaction / 7.1: Swern oxidation;

DOI:10.1021/ol060347s

Reference yield:

(4R,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one (888488-12-8) → (3R,4R,5R,6R,8R,10S,11S,12S,13S)-3,11-bis[tert-butyldimethylsilyloxy]-5-triethylsilyloxy-2,4,6,8,10,12-hexamethyl-13-[4-methoxy-benzyloxy]pentadeca-7,9-dione (888488-07-1)

Guidance literature:

Multi-step reaction with 6 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

6.1: 88 percent / DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 0 °C

With sodium tetrahydroborate; oxalyl dichloride; trifluorormethanesulfonic acid; hydrogen; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; W-2 Raney nickel; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 4.1: Dess-Martin oxidation / 5.2: aldol reaction / 6.1: Swern oxidation;

DOI:10.1021/ol060347s

upstream raw materials:

(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

(4R,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-one

(3S,4S,5R,6R)-7-benzyloxy-5-tert-butyldimethylsilyloxy-4,6-dimethylheptan-3-ol

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