(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

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Chemical Name:(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one
CAS No.:847049-80-3
Molecular Formula:C₃₂H₄₂O₃Si
Molecular Weight:502.769
Hs Code.:

Synonyms:(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

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Chemical Property of (1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

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Technology Process of (1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

There total 12 articles about (1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-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: 79.0%

: 847049-79-0
(2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-hydroxyhept-1-enyl]cyclopentyl}but-2-enoic acid

: 847049-80-3
(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Guidance literature:: (2E,4R)-4-[(tert-butyldiphenylsilyl)oxy]-4-{(1R,2S)-2-[(1E,6S)-6-hydroxyhept-1-enyl]cyclopentyl}but-2-enoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 8h; Inert atmosphere;

With dmap; In tetrahydrofuran; toluene; at 110 ℃; for 16h; Inert atmosphere;
DOI:10.1002/ejoc.200901233

Reference yield:

: cis-2-carbomethoxy cyclopentane-1-carboxylic acid

: 847049-80-3
(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 92 percent / t-BuOK / tetrahydrofuran / 1 h / 0 - 20 °C

2.1: 60 percent / BH₃*SMe₂ / tetrahydrofuran / 12 h / -20 - 20 °C

3.1: 96 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / -60 - 20 °C

4.1: 75 percent / CrCl₂ / tetrahydrofuran; dioxane / 72 h / 25 °C

5.1: aq. Cs₂CO₃ / [Pd(dppf)Cl₂*CH₂Cl₂] / dimethylformamide; tetrahydrofuran / 6 h / 30 °C

6.1: 85 percent / LiAlH₄ / diethyl ether / 3 h / 0 - 25 °C

7.1: 89 percent / (COCl)2; DMSO; DIEA / CH₂Cl₂ / -60 - 20 °C

8.1: Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 0.25 h / 23 °C

8.2: toluene / 24 h / 23 °C

9.1: 96 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

10.1: PPh₃ / Pd(PPh₃)4 / toluene / 0.33 h / 20 °C

10.2: 33 percent / toluene / 1 h / 110 °C

11.1: 98 percent / 2-methyl-2-butene; NaO₂Cl; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 24 h / 20 °C

12.1: 78 percent / aq. DDQ / CH₂Cl₂ / 12 h / 20 °C

13.1: Et₃N / tetrahydrofuran / 8 h / 20 °C

14.1: DMAP / toluene; tetrahydrofuran / 16 h / Heating

With 1H-imidazole; chromium dichloride; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; potassium tert-butylate; zinc trifluoromethanesulfonate; caesium carbonate; (+)-N-methylephedrine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [1,1'-bis(diphenylphosphino)-ferrocene]palladium(II) chloride-dichlormethane complex; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: Swern oxidation / 7.1: Swern oxidation;
DOI:10.1055/s-2004-835669

Reference yield:

: 847049-73-4
(1R,2S)-2-{(1E,6S)-6-[(4-methoxybenzyl)oxy]hept-1-enyl}cyclopentanecarbaldehyde

: 847049-80-3
(1R,6S,11aS,14aR)-1-[(tert-butyldiphenylsilyl)oxy]-6-methyl-1,6,7,8,9,11a,12,13,14,14a-decahydro-4H-cyclopenta[f]oxacyclotridecin-4-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Zn(OTf)2; (+)-N-methylephedrine; Et₃N / toluene / 0.25 h / 23 °C

1.2: toluene / 24 h / 23 °C

2.1: 96 percent / imidazole / dimethylformamide / 12 h / 0 - 20 °C

3.1: PPh₃ / Pd(PPh₃)4 / toluene / 0.33 h / 20 °C

3.2: 33 percent / toluene / 1 h / 110 °C

4.1: 98 percent / 2-methyl-2-butene; NaO₂Cl; aq. NaH₂PO₄ / 2-methyl-propan-2-ol / 24 h / 20 °C

5.1: 78 percent / aq. DDQ / CH₂Cl₂ / 12 h / 20 °C

6.1: Et₃N / tetrahydrofuran / 8 h / 20 °C

7.1: DMAP / toluene; tetrahydrofuran / 16 h / Heating

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; zinc trifluoromethanesulfonate; (+)-N-methylephedrine; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1055/s-2004-835669