(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one

Base Information

• Chemical Name: (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one
• CAS No.: 1352492-31-9
• Molecular Formula: C₂₈H₃₀O₃Si
• Molecular Weight: 442.63
• Mol file: 1352492-31-9.mol

Synonyms:(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one

Chemical Property of (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one

There total 1 articles about (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-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: 74.0%

phenylacetylene (536-74-3) + (3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide (478491-15-5) → (S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one (1352492-31-9)

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;

(3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.10.006

Reference yield: 85.0%

(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one (1352492-31-9) → (S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyl-2H-pyran-4(3H)-one (1352492-32-0)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 0.5h; Darkness; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.10.006

Reference yield:

(S)-6-(tert-butyldiphenylsilyloxy)-5-hydroxy-1-phenylhex-1-yn-3-one (1352492-31-9) → (2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate (1352492-34-2)

Guidance literature:

Multi-step reaction with 4 steps

1: silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Darkness; Inert atmosphere

2: palladium 10% on activated carbon; hydrogen; triethylamine / ethanol / 6 h / 20 °C / Inert atmosphere

3: sodium tetrahydroborate; cerium(III) chloride / methanol / -78 °C / Inert atmosphere

4: triphenylphosphine; diethylazodicarboxylate / toluene / 0.25 h / 20 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride; palladium 10% on activated carbon; hydrogen; silver trifluoromethanesulfonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In methanol; ethanol; dichloromethane; toluene; 4: Mitsunobu reaction;

DOI:10.1016/j.tetasy.2011.10.006

upstream raw materials:

phenylacetylene

(3S)-4-(tert-butyldiphenylsilanyloxy)-hydroxy-N-methoxy-N-methylbutyramide

Downstream raw materials:

(2S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyldihydro-2H-pyran-4(3H)-one

(2S,4S,6R)-2-((tert-butyldiphenylsilyloxy)methyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

(2S,4S,6R)-2-(hydroxymethyl)-6-phenyltetrahydro-2H-pyran-4-yl 4-nitrobenzoate

(Z,2R,4R,6S)-2-phenyl-6-styryltetrahydro-2H-pyran-4-ol