(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

Base Information

Chemical Name:(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one
CAS No.:1415730-26-5
Molecular Formula:C₂₁H₃₆O₄Si
Molecular Weight:380.6
Hs Code.:

Synonyms:(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

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Chemical Property of (3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

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Technology Process of (3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

There total 5 articles about (3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-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: 76.0%

: 1415730-31-2
(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhex-1-yne

: 1415730-26-5
(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

Guidance literature:: With mercury(II) diacetate; pyridinium p-toluenesulfonate; In tetrahydrofuran; at 45 ℃; for 5h; pH=7; Inert atmosphere;
DOI:10.1016/j.tet.2012.10.008

Reference yield:

: 1415730-30-1
(5S)-6-(4-methoxybenzyl)oxy-5-methyl-3-oxohex-1-yne

: 1415730-26-5
(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 2 h / -30 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 7.5 h / -78 °C / Inert atmosphere

3: pyridinium p-toluenesulfonate; mercury(II) diacetate / tetrahydrofuran / 5 h / 45 °C / pH 7 / Inert atmosphere

With 2,6-dimethylpyridine; mercury(II) diacetate; dimethyl sulfide borane; pyridinium p-toluenesulfonate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tet.2012.10.008

Reference yield:

: 212051-35-9
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

: 1415730-26-5
(3S,5S)-3-(tert-butyldimethylsilyloxy)-6-((4-methoxybenzyl)oxy)-5-methylhexan-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

2: pyridine / 9 h / 0 °C / Inert atmosphere

3: dimethyl sulfoxide / 18 h / 60 °C / Inert atmosphere

4: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere

5: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

6: phthalic acid dimethyl ester; water / dichloromethane / 4 h / 20 °C / Inert atmosphere

7: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 2 h / -30 °C / Inert atmosphere

8: 2,6-dimethylpyridine / dichloromethane / 7.5 h / -78 °C / Inert atmosphere

9: pyridinium p-toluenesulfonate; mercury(II) diacetate / tetrahydrofuran / 5 h / 45 °C / pH 7 / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; phthalic acid dimethyl ester; mercury(II) diacetate; water; dimethyl sulfide borane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 5: |Grignard Reaction;
DOI:10.1016/j.tet.2012.10.008