3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

Base Information

Chemical Name:3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane
CAS No.:193481-16-2
Molecular Formula:C₂₅H₄₂O₅Si
Molecular Weight:450.691
Hs Code.:

Synonyms:3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

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Chemical Property of 3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

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Technology Process of 3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

There total 1 articles about 3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane 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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 193481-16-2
3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 92 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

2.1: tBuLi / diethyl ether; pentane / 0.33 h / -78 °C

2.2: 65 percent / diethyl ether; pentane / 0.5 h / -78 °C

With tert.-butyl lithium; triethylamine; In diethyl ether; dichloromethane; pentane; 1.1: Etherification / 2.1: Metallation / 2.2: Substitution;
DOI:10.1055/s-2000-8223

Reference yield:

: 193481-16-2
3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

: 193481-29-7
C₂₉H₃₀O₇

Guidance literature:: Multi-step reaction with 15 steps

1: BH₃*SMe₂, chiral oxazaborolidine derivative / tetrahydrofuran / 0.17 h / -10 °C

2: TBAF / tetrahydrofuran / 0.17 h / 0 °C

4: BHT / toluene / 48 h / 210 °C

5: 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

6: OsO₄, NMO / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 23 h / Ambient temperature

7: 81 percent / PPTS / benzene / 3 h / Heating

8: 1.) NaBH₃CN, TfOH, 4 Angstroem molecular sieves, 2.) NaH, TBAI, 3.) DDQ / 1.) DMF, rt, 12 h, 2.) THF, rt, 27 h, 3.) CH₂Cl₂, H₂O, rt, 2 h

9: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

10: 87 percent / PTS / ethane-1,2-diol; tetrahydrofuran / 31 h / 50 °C

11: 70 percent / TfOH / diethyl ether / 22 h / Ambient temperature

12: 95 percent / TBAF / tetrahydrofuran / 12 h / 0 - 20 °C

13: 84 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂ / 12 h / Ambient temperature

14: LDA / tetrahydrofuran / 0.42 h / -78 °C

15: TMSOTf / tetrahydrofuran / 2 h / 0 - 20 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; dipyridinium dichromate; N-methyl-2-indolinone; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methyl-phenol; dimethylsulfide borane complex; 3 A molecular sieve; 4 A molecular sieve; chiral oxazaborolidine derivative; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethylene glycol; toluene; tert-butyl alcohol; benzene;
DOI:10.1055/s-1997-3271

Reference yield:

: 193481-16-2
3-[2',2'-Dimethyl-5'-(prop-2''-enyl)-1',3'-dioxan-5'-yl]-1-(2'''-triisopropylsilyloxyfuran-4'''-yl)-1-oxopropane

: (2aR,3S,4aS,7aS,10R,10aS,10bS)-10a-benzyloxymethyl-10-hydroxy-3-(p-methoxybenzyl)oxyperhydronaphtho(1,8-bc:4,4a-c')difuran-5,8-dione

Guidance literature:: Multi-step reaction with 17 steps

1: BH₃*SMe₂, chiral oxazaborolidine derivative / tetrahydrofuran / 0.17 h / -10 °C

2: TBAF / tetrahydrofuran / 0.17 h / 0 °C

4: BHT / toluene / 48 h / 210 °C

5: 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

6: OsO₄, NMO / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 23 h / Ambient temperature

7: 81 percent / PPTS / benzene / 3 h / Heating

8: 1.) NaBH₃CN, TfOH, 4 Angstroem molecular sieves, 2.) NaH, TBAI, 3.) DDQ / 1.) DMF, rt, 12 h, 2.) THF, rt, 27 h, 3.) CH₂Cl₂, H₂O, rt, 2 h

9: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

10: 87 percent / PTS / ethane-1,2-diol; tetrahydrofuran / 31 h / 50 °C

11: 70 percent / TfOH / diethyl ether / 22 h / Ambient temperature

12: 95 percent / TBAF / tetrahydrofuran / 12 h / 0 - 20 °C

13: 84 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂ / 12 h / Ambient temperature

14: LDA / tetrahydrofuran / 0.42 h / -78 °C

15: TMSOTf / tetrahydrofuran / 2 h / 0 - 20 °C

16: 50 percent / TBHP, TBAF / dimethylsulfoxide / 1 h / Ambient temperature

17: 56 percent / sodium phenylseleno(triethoxy)borate / acetic acid; ethanol / 0.33 h / Ambient temperature

With 2,6-dimethylpyridine; tert.-butylhydroperoxide; osmium(VIII) oxide; dipyridinium dichromate; N-methyl-2-indolinone; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; 2,6-di-tert-butyl-4-methyl-phenol; dimethylsulfide borane complex; 3 A molecular sieve; 4 A molecular sieve; chiral oxazaborolidine derivative; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; sodium phenylseleno(triethyl)borate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethylene glycol; acetic acid; dimethyl sulfoxide; toluene; tert-butyl alcohol; benzene;
DOI:10.1055/s-1997-3271