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

Base Information

Chemical Name:(2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-one
CAS No.:1188304-34-8
Molecular Formula:C₂₈H₄₀O₃Si
Molecular Weight:452.709
Hs Code.:

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

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Chemical Property of (2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-one

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Technology Process of (2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-one

There total 9 articles about (2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-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: 80.0%

: 1188304-33-7
(2R,3S,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyltetrahydro-2H-pyran-3-ol

: 1188304-34-8
(2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-one

Guidance literature:: With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 18h; Molecular sieve;
DOI:10.1016/j.tetlet.2009.07.041

Reference yield:

: 191593-14-3
4,6-O-di(tert-butyl)silanediyl-D-glucal

: 1188304-34-8
(2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: mercury(II) diacetate / 96 h / 65 °C / Sealed tube

2.1: toluene / 5 h / 185 °C / Sealed tube

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C

3.2: 0.33 h

4.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C

6.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0.5 h / 20 °C

7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 18 h / 20 °C / Molecular sieve

With 1H-imidazole; dmap; n-butyllithium; tetrapropylammonium perruthennate; palladium 10% on activated carbon; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.1: |Claisen Rearrangement / 3.2: |Wittig Olefination;
DOI:10.1016/j.tet.2012.08.094

Reference yield:

: 1188304-30-4
(4aR,8R,8aS)-2,2-di-tert-butyl-8-(vinyloxy)-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3,2]dioxasiline

: 1188304-34-8
(2R,6S)-2-((tert-butyldiphenylsilyloxy)methyl)-6-hexyldihydro-2H-pyran-3(4H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: toluene / 5 h / 185 °C / Sealed tube

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 0.33 h

3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 h / 20 °C

5.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 0.5 h / 20 °C

6.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 18 h / 20 °C / Molecular sieve

With 1H-imidazole; dmap; n-butyllithium; tetrapropylammonium perruthennate; palladium 10% on activated carbon; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: |Claisen Rearrangement / 2.2: |Wittig Olefination;
DOI:10.1016/j.tet.2012.08.094