Boron trifluoride etherate → (2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

HRID 46187ノート

反応式

HRID 46187 の反応式
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C:10]1([C:41]1[CH:46]=[CH:45][C:44]([Cl:47])=[C:43]([CH2:48][O:49][Si:50]([CH:57]([CH3:59])[CH3:58])([CH:54]([CH3:56])[CH3:55])[CH:51]([CH3:53])[CH3:52])[CH:42]=1)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[Cl:47][C:44]1[CH:45]=[CH:46][C:41]([CH:10]2[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C@H:13]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[O:11]2)=[CH:42][C:43]=1[CH2:48][O:49][Si:50]([CH:57]([CH3:59])[CH3:58])([CH:51]([CH3:53])[CH3:52])[CH:54]([CH3:56])[CH3:55]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 67287055(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

生成物 1

HCID 67287190(2-Chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-10 °C

実験手順

To a stirred −50° C. solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)tetra-hydro-2H-pyran-2-ol (198 mmol) from Step 4 in dichloromethane (500 mL) was added triethylsilane (63 mL, 396 mmol) followed by boron trifluoride diethyl etherate (50 mL, 396 mmol) at a rate such that the reaction temperature was maintained between −40 and −50° C. The solution was allowed to warm to −10° C. over 2 h prior to quenching with saturated potassium carbonate solution. After removal of organic volatiles under reduced pressure, the residue was partitioned between ethyl acetate and water. Following extraction of the aqueous layer with ethyl acetate, the combined organic layers were washed with water prior to drying over magnesium sulfate. Filtration and concentration under reduced pressure yielded the title compound as a yellow oil which was used without further purification.

後処理

  1. temperaturewas maintained between −40 and −50° C
  2. customto quenching with saturated potassium carbonate solution
  3. customAfter removal of organic volatiles under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and water
  5. extractionextraction of the aqueous layer with ethyl acetate
  6. washthe combined organic layers were washed with water
  7. dry with materialto drying over magnesium sulfate
  8. filtrationFiltration and concentration under reduced pressure

出典と根拠

ORDレコード
ord-397203220aa746e9b261b147a0ed6f68
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

反応ノート

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