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CAS No. : | 146952-73-0 | MDL No. : | MFCD21362363 |
Formula : | C24H28O2Si | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AUBBTJZRJRFGME-UHFFFAOYSA-N |
M.W : | 376.56 | Pubchem ID : | 11047063 |
Synonyms : |
|
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340 | UN#: | |
Hazard Statements: | H302 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With 1H-imidazole In N,N-dimethyl-formamide for 24h; | |
53% | With 1H-imidazole In N,N-dimethyl-formamide 0 deg C, 30 min, r.t., 20 h; | |
51% | With 1H-imidazole In tetrahydrofuran at 20℃; Inert atmosphere; |
42% | With 1H-imidazole In N,N-dimethyl-formamide at 50℃; for 16h; | |
38% | With 1H-imidazole In N,N-dimethyl-formamide for 21h; Inert atmosphere; | |
With sodium hydride 1.) THF, RT, 30 min, 2.) THF, RT, 4 h; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With manganese(IV) oxide In dichloromethane at 20℃; for 12h; | |
87% | With dipyridinium dichromate In dichloromethane for 3h; Ambient temperature; | |
74% | With 4-methylmorpholine N-oxide In acetone for 0.416667h; |
Multi-step reaction with 2 steps 1: imidazole / dimethylformamide / 20 °C 2: 90 percent / CrO3; H5IO6 / CH2Cl2; acetonitrile / 1 h / -78 °C | ||
1.86 g | With manganese(IV) oxide In chloroform for 6h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; triphenylphosphine In tetrahydrofuran for 13h; Ambient temperature; Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In dichloromethane; acetonitrile at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C 7.1: 90 percent / Pseudomonas cepacia Lipase / acetone; butan-1-ol; hexane / 35 h 8.1: TBAF |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C 7.1: Pseudomonas cepacia Lipase / acetone; butan-1-ol; hexane / 35 h 7.2: 0.31 g / aq. LiOH / methanol / 1 h 8.1: 77 percent / TBAF / tetrahydrofuran / 5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C 7.1: 90 percent / Pseudomonas cepacia Lipase / acetone; butan-1-ol; hexane / 35 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C 7.1: Pseudomonas cepacia Lipase / acetone; butan-1-ol; hexane / 35 h 7.2: 0.31 g / aq. LiOH / methanol / 1 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h 2.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C 3.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C 4.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h 5.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C 5.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C 6.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C 7.1: 90 percent / Pseudomonas cepacia Lipase / acetone; butan-1-ol; hexane / 35 h 8.1: 31 percent / 1-[3-(DMA)propyl]-3-ethylcarbodiimide hydrochloride; (dimethylamino)pyridine / CH2Cl2 / 6 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 96 percent / LiAlH4 / diethyl ether / 0 deg C, 15 min; RT, 30 min; reflux, 16 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h 4: 1) NaH / 1) THF, reflux, 30 min, 2) THF, RT, 24 h then reflux, 1 h and overnight, RT 5: 63 percent / diethyl ether 6: 90 percent / LiAlH4 / tetrahydrofuran / 5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h 4: 1) NaH / 1) THF, 0 deg C, 15 min then RT, 15 min and 70 deg C, 30 min, 2) THF, RT, 1.5 h then reflux, 1 h and RT, 20 h, then reflux, 4 h 5: Bu4NF / tetrahydrofuran / 24 h / Ambient temperature 6: 94 percent / PPh3, CBr4 / tetrahydrofuran / 27 h | ||
Multi-step reaction with 6 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 96 percent / LiAlH4 / diethyl ether / 0 deg C, 15 min; RT, 30 min; reflux, 16 h 4: 1) NaH / 1) THF, reflux, 30 min, 2) THF, reflux, 23 h 5: 84 percent / LiBF4 / H2O; acetonitrile / 49 h / 70 °C 6: 94 percent / PPh3, CBr4 / tetrahydrofuran / 27 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h 4: 1) NaH / 1) THF, 0 deg C, 15 min then RT, 15 min and 70 deg C, 30 min, 2) THF, RT, 1.5 h then reflux, 1 h and RT, 20 h, then reflux, 4 h 5: Bu4NF / tetrahydrofuran / 24 h / Ambient temperature | ||
Multi-step reaction with 5 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 96 percent / LiAlH4 / diethyl ether / 0 deg C, 15 min; RT, 30 min; reflux, 16 h 4: 1) NaH / 1) THF, reflux, 30 min, 2) THF, reflux, 23 h 5: 84 percent / LiBF4 / H2O; acetonitrile / 49 h / 70 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 96 percent / LiAlH4 / diethyl ether / 0 deg C, 15 min; RT, 30 min; reflux, 16 h 4: 1) NaH / 1) THF, reflux, 30 min, 2) THF, reflux, 23 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h 4: 1) NaH / 1) THF, reflux, 30 min, 2) THF, RT, 24 h then reflux, 1 h and overnight, RT |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h 4: 1) NaH / 1) THF, reflux, 30 min, 2) THF, RT, 24 h then reflux, 1 h and overnight, RT 5: 63 percent / diethyl ether |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Ph3P, Br2 / tetrahydrofuran / 13 h / Ambient temperature 2: 1) BuLi (1.5M in hexane, (iPr)2NH / 1) THF, 0 deg C, 15 min, 2) THF, -78 deg C, 30 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 0 deg C, 2 h; RT, 14.5 h 4: 1) NaH / 1) THF, 0 deg C, 15 min then RT, 15 min and 70 deg C, 30 min, 2) THF, RT, 1.5 h then reflux, 1 h and RT, 20 h, then reflux, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 59 percent / NaH / tetrahydrofuran / 18 h / Heating 5: 86 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature 6: 82 percent / Br4C, Ph3P / tetrahydrofuran / 21 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature 4: 64 percent / NaH / tetrahydrofuran / 23 h / Heating 5: 96 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature 6: 51 percent / Br4C, Ph3P / tetrahydrofuran / 6 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 72 percent / NaH / tetrahydrofuran / 17 h / Heating 5: 90 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 59 percent / NaH / tetrahydrofuran / 18 h / Heating 5: 86 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature 4: 64 percent / NaH / tetrahydrofuran / 23 h / Heating 5: 96 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature 4: 85 percent / NaH / tetrahydrofuran / 17 h / Heating 5: 93 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 72 percent / NaH / tetrahydrofuran / 17 h / Heating 5: 90 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature 6: 71 percent / Br4C, PPh3 / tetrahydrofuran / 44 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature 4: 85 percent / NaH / tetrahydrofuran / 17 h / Heating 5: 93 percent / TBAF / tetrahydrofuran / 24 h / Ambient temperature 6: 70 percent / Br4C, PPh3 / tetrahydrofuran / 44 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature 4: 64 percent / NaH / tetrahydrofuran / 23 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 93 percent / NaBH4 / tetrahydrofuran; methanol / 20 h / Ambient temperature 4: 85 percent / NaH / tetrahydrofuran / 17 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 72 percent / NaH / tetrahydrofuran / 17 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h 3: 92 percent / NaBH4 / tetrahydrofuran; methanol / 18 h / Ambient temperature 4: 59 percent / NaH / tetrahydrofuran / 18 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 87 percent / PDC / CH2Cl2 / 3 h / Ambient temperature 2: 1.) (i-Pr)2NH, BuLi / 1.) THF, 0 deg C, 15 min; 2.) THF, -78 deg C, 45 min; 3.) THF, -78 deg C, 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 1 h 2: NaI / acetone / 16 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 1 h 2: NaI / acetone / 16 h / Heating 3: 49 percent / Cs2CO3 / dimethylformamide / 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 1 h 2: NaI / acetone / 16 h / Heating 3: 15 percent / Cs2CO3 / dimethylformamide / 3 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 7h; | Deprotection of TBS Ethers; General Procedure General procedure: A solution of the TBS ether (2 mmol) in MeOH (4 mL) was treated with NaAuCl4·2H2O (4.0 mg, 0.01 mmol, 0.005 equiv) at r.t. When the starting material had disappeared (TLC), mixture was diluted with EtOAc (10 mL) and filtered through activated alumina. The solution was then concentrated in vacuo and the resulting residue was purifiedby flash column chromatography. |
94% | With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 12h; chemoselective reaction; | Hf(OTf)4-Catalyzed Desilylation; General Procedure General procedure: To a solution of silyl ether in MeOH (AR grade) was added Hf(OTf)4 (0.02-3 mol%). The reaction ([substrate] = 0.15 M) was stirred at room temperature for 0.5-16 h and monitored by TLC. Upon completion, excess triethylamine was added to neutralize the Lewis acid. The solution was concentrated in vacuo. Flash column chromatography on silica gel afforded desilylated product in pure form. |
94% | With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 12h; chemoselective reaction; | 6 Example 6: Removal of protecting groups for 4-[(tert-butyldimethylsilyloxy)methyl]-1-[(tert-butylphenylsilyloxy)methyl]benzene (32) Add Hf(OTf)4 (15 mg, to a conventional methanol solution (13 mL) containing 32 (980 mg, 2 mmol).0.02 mmol), stirred at 20 ° C for 12 hours. After the end of the reaction, Hf(OTf)4 was neutralized by adding 10 equivalents of triethylamine to the reaction.The reaction solution was concentrated under reduced pressure and the crude product was purified by flash column chromatography(Petroleum ether: ethyl acetate = 40:1) purified to give an oil4 - [(tert-butyldiphenylsilyloxy) methyl] phenyl methanol (32 ') 705mg, 94% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 5h; chemoselective reaction; | Hf(OTf)4-Catalyzed Desilylation; General Procedure General procedure: To a solution of silyl ether in MeOH (AR grade) was added Hf(OTf)4 (0.02-3 mol%). The reaction ([substrate] = 0.15 M) was stirred at room temperature for 0.5-16 h and monitored by TLC. Upon completion, excess triethylamine was added to neutralize the Lewis acid. The solution was concentrated in vacuo. Flash column chromatography on silica gel afforded desilylated product in pure form. |
95% | With hafnium tetrakis(trifluoromethanesulfonate) In methanol at 20℃; for 5h; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: [4-([tert-butyl(diphenyl)silyl]oxy}methyl)phenyl]methanol With methanesulfonyl chloride; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: indole-6-carboxylic acid methyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 °C / Inert atmosphere 5.1: sodium acetate / ethanol / 10 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 0 - 20 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / Inert atmosphere 3.1: methanesulfonyl chloride; triethylamine / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 1 h / -78 °C / Inert atmosphere 5.1: sodium acetate / ethanol / 10 h / Inert atmosphere 6.1: hydrazine hydrate / ethanol / 7 h / Reflux; Inert atmosphere |