(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

Base Information

Chemical Name:(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one
CAS No.:151936-92-4
Molecular Formula:C₂₆H₃₂O₄Si
Molecular Weight:436.623
Hs Code.:

Synonyms:(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

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Chemical Property of (4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

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Technology Process of (4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

There total 13 articles about (4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-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: 61.0%

: (1S,3R,4R,5S,6S)-3-<(tert-Butyldiphenylsilyl)oxy>-4,5-(isopropylidenedioxy)-6-<(methylsulfonyl)oxy>cycloheptan-1-ol

: 151936-92-4
(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1.) -60 deg C, 20 min, 2.) -60 deg C to room temp., 10 min then room temp., 2 h;
DOI:10.1021/jo00077a049

Reference yield:

: 111795-52-9
(3R,5R,7S)-3,7-dihydroxy-5-((tert-butyldimethylsilyl)oxy)cyclohept-1-ene

: 151936-92-4
(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

Guidance literature:: Multi-step reaction with 8 steps

1: Pseudomona cepacia lipase

2: imidazole / dimethylformamide

3: OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; H₂O

4: TsOH

5: KOH / methanol

6: MsCl, Et₃N / CH₂Cl₂

7: pyridinium tosylate / methanol

8: PDC / CH₂Cl₂

With 1H-imidazole; potassium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; Pseudomona cepacia lipase; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(98)00145-1

Reference yield:

: 134734-52-4
(1R,4S,6S)-4-acetoxy-6-[(tert-butyldimethylsilyl)oxy]-2-cyclohepten-1-ol

: 151936-92-4
(4R,5R,6R)-6-[(tert-Butyldiphenylsilyl)oxy]-4,5-(isopropylidenedioxy)-2-cyclohepten-1-one

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / dimethylformamide

2: OsO₄, N-methylmorpholine N-oxide / tetrahydrofuran; H₂O

3: TsOH

4: KOH / methanol

5: MsCl, Et₃N / CH₂Cl₂

6: pyridinium tosylate / methanol

7: PDC / CH₂Cl₂

With 1H-imidazole; potassium hydroxide; osmium(VIII) oxide; dipyridinium dichromate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; methanesulfonyl chloride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(98)00145-1