(R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

Base Information

Chemical Name:(R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one
CAS No.:1352286-67-9
Molecular Formula:C₂₅H₃₂O₃Si
Molecular Weight:408.613
Hs Code.:

Synonyms:(R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

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Chemical Property of (R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

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Technology Process of (R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

There total 2 articles about (R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-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%

: 1352286-66-8
(2R,3R)-1-(tert-butyldiphenylsilyloxy)-2-methylhex-5-en-3-yl methacrylate

: 1352286-67-9
(R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,3,5,6-tetrafluoro-1,4-benzoquinone; In toluene; at 60 ℃; for 18h; Inert atmosphere;
DOI:10.1021/ol203161u

Reference yield:

: 112897-06-0
(2R,3R)-1-(tert-butyldiphenylsilyloxy)-2-methylhex-5-en-3-ol

: 1352286-67-9
(R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,3,5,6-tetrafluoro-1,4-benzoquinone / toluene / 18 h / 60 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,3,5,6-tetrafluoro-1,4-benzoquinone; triethylamine; In dichloromethane; toluene;
DOI:10.1021/ol203161u

Reference yield:

: 1352286-67-9
(R)-6-((R)-1-(tert-butyldiphenylsilyloxy)propan-2-yl)-3-methyl-5,6-dihydro-2H-pyran-2-one

: N-(2,4-dimethoxybenzyl)tirandamycin C

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

2.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

3.1: diisopinocampheylborane / diethyl ether / 5 h / 0 °C / Inert atmosphere

3.2: 24 h / -78 - 20 °C / Inert atmosphere

3.3: 1 h / 20 °C / Inert atmosphere

4.1: diethyl ether / 4 h / -78 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

6.1: Stewart-Grubbs catalyst / dichloromethane / 12 h / Inert atmosphere; Reflux

7.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

7.2: 12 h / 20 °C / Inert atmosphere

With Stewart-Grubbs catalyst; potassium tert-butylate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; diisopinocampheylborane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ol203161u