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CAS No. : | 75853-49-5 | MDL No. : | MFCD10000650 |
Formula : | C14H28O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OQWNKUAZQSLNSR-UHFFFAOYSA-N |
M.W : | 212.37 | Pubchem ID : | 3018619 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
98% | With pyridinium chlorochromate In dichloromethane at 20℃; for 24h; | |
85% | With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 0℃; for 4h; | |
84% | With pyridinium chlorochromate In dichloromethane for 2h; |
With dipyridinium dichromate; 3 A molecular sieve In dichloromethane for 2h; Ambient temperature; | ||
With Dess-Martin periodane In dichloromethane at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66.04% | With periodic acid In tetrahydrofuran; diethyl ether for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With triethylamine In dichloromethane at 25℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 93 percent / LiAlH4 / diethyl ether / 2 h / 0 °C 2: 98 percent / pyridinium chlorochromate / CH2Cl2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 96 percent / Et3N / CH2Cl2 / 2 h / 25 °C 2: aq. HCl / 1,2-dimethoxy-ethane / 24 h / 90 °C 3: aq. NaOH / 1,2-dimethoxy-ethane / 2 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 96 percent / Et3N / CH2Cl2 / 2 h / 25 °C 2: aq. HCl / 1,2-dimethoxy-ethane / 24 h / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 1.) Mg, 2.) dilithium tetrachlorocuprate / 1) THF, 2.) THF, -10 deg C, 4 h 2: 1.) NaBH4, Hg(OAc)2, 2.) aq. H2O2, aq. NaOH / 1) THF, 16 h, room temperature; 2) THF, 70 deg C, 1 h 3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: tetrahydrofuran 2: pyridinium chlorochromate / CH2Cl2 | ||
Multi-step reaction with 2 steps 1: 1) Mg / 1) ether, 2) ether, a) 0 deg C to rt, 4 h, b) overnight 2: 83.33 percent / pyridinium chlorochromate / CH2Cl2 / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) NaBH4, Hg(OAc)2, 2.) aq. H2O2, aq. NaOH / 1) THF, 16 h, room temperature; 2) THF, 70 deg C, 1 h 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 100 percent / LiAlH4 / tetrahydrofuran 2: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 74 percent / H2 / 10percent Pd/C / ethanol / Ambient temperature 2: 100 percent / LiAlH4 / tetrahydrofuran 3: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C 3: diethyl ether / 4.5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C 3: diethyl ether / 4.5 h / 0 - 20 °C 4: Li(1+)*AlH4(1-)*3C4H10O / tetrahydrofuran; dichloromethane / 4 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C 3: diethyl ether / 4.5 h / 0 - 20 °C 4: Li(1+)*AlH4(1-)*3C4H10O / tetrahydrofuran; dichloromethane / 4 h / -78 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere 2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 % ee | With 2,2,5,7,8-pentamethylchroman-6-ol; mesitylcopper(I); (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In tetrahydrofuran; N,N-dimethyl-formamide at -60℃; for 40h; Inert atmosphere; Overall yield = 92 %; Overall yield = 67.6 mg; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With 2,2,5,7,8-pentamethylchroman-6-ol; mesitylcopper(I); (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In tetrahydrofuran; N,N-dimethyl-formamide at -60℃; for 40h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogen bromide / water; toluene / 48 h / Reflux 2: dilithium tetrachlorocuprate / tetrahydrofuran / 20 h / -78 °C 3: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 4 h / -78 - 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dilithium tetrachlorocuprate / tetrahydrofuran / 20 h / -78 °C 2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 4 h / -78 - 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C 10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C 10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C 11.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C 10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C 11.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / 20 °C 12.1: triethylamine / tetrahydrofuran / 1.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 9 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 10 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C 10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 11 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C 10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C 11.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 12 steps 1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C 4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C 5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C 5.2: 20 h / 20 °C 6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C 7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C 9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C 10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C 11.1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 18 h / 20 °C 12.1: triethylamine / tetrahydrofuran / 1.17 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: titanium tetrachloride / dichloromethane / 42 h / -78 °C 2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With titanium tetrachloride In dichloromethane at -78℃; for 42h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93.5% | With ozone In dichloromethane at -55℃; | 2.4 Step four dilute ozonation Dichloromethane (331 ml) and D (41.4 g) were successively added to the reaction vessel, and the temperature was lowered to -55°C. Under vigorous stirring, ozone was introduced into the reaction vessel. After the GC reaction was completed, ozone was stopped and ozone was slowly added dropwise. Ethyl ether, without drastic increase in temperature after dropping, the system temperature 10 ~ 30 ° C, adding water 82ml, liquid separation, dichloromethane phase was dried over anhydrous sodium sulfate, and concentrated to give a liquid product TM 38.9g, gas phase mass spectrometry purity 99.0% , Yield 93.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With recombinant carboxylic acid reductase from Mycobacterium marinum; ATP; NADPH; magnesium chloride In aq. phosphate buffer; hexane at 30℃; for 8h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triphenylphosphine / dichloromethane / 0.5 h / -10 - -5 °C 1.2: 3 h / -10 - -5 °C 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 - 0 °C 2.2: 1.5 h / -78 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: triphenylphosphine / dichloromethane / 0.5 h / -10 - -5 °C 1.2: 3 h / -10 - -5 °C 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 - 0 °C 2.2: 1.5 h / -78 - 20 °C 3.1: sodium hydroxide / <i>tert</i>-butyl alcohol; water / 6 h / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: triphenylphosphine / dichloromethane / 0.5 h / -10 - -5 °C 1.2: 3 h / -10 - -5 °C 2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 - 0 °C 2.2: 1.5 h / -78 - 20 °C 3.1: sodium hydroxide / <i>tert</i>-butyl alcohol; water / 6 h / 60 °C 4.1: hydrogen; quinoline / ethanol / 24 h / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94 mg | Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at -10 - -5℃; for 0.5h; Stage #2: 12-methyltridecan-1-al In dichloromethane at -10 - -5℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: palladium on activated carbon; hydrogen / methanol / 3 h / 20 °C 2: Dess-Martin periodane / dichloromethane / 1 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With α‑dioxygenase from Crocosphaera subtropica In aq. phosphate buffer Enzymatic reaction; |