Water → (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol

HRID 2204969ノート

反応式

HRID 2204969 の反応式
[CH2:1]([O:17][CH2:18][C@H:19]([OH:22])[CH2:20][OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:23][C:24]([Si:27](Cl)([CH3:29])[CH3:28])([CH3:26])[CH3:25].CCN(CC)CC.O>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:27]([O:21][CH2:20][C@@H:19]([OH:22])[CH2:18][O:17][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([C:24]([CH3:26])([CH3:25])[CH3:23])([CH3:29])[CH3:28]

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11758911(2R)-3-(Hexadecyloxy)-1,2-propanediol

生成物 1

HCID 10960980(S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (R)-3-(hexadecyloxy)propane-1,2-diol (1 eq), TBDMSCl (1.4 eq), NEt3 (1.4 eq) and DMAP (0.05 eq) in DCM (0.5 M) was stirred at 25° C. over night. The reaction was diluted with DCM and was with H2O twice, and the aqueous phase was back extracted with DCM. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate and concentrated en vaccuo. The resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-20% EtOAc/Hex to give (S)-1-(tert-butyldimethylsilyloxy)-3-(hexadecyloxy)propan-2-ol as a colorless oil.

後処理

  1. extractionthe aqueous phase was back extracted with DCM
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated en vaccuo
  5. customThe resulting crude was purified by flash chromatography on a COMBIFLASH® system (ISCO)

出典と根拠

ORDレコード
ord-203199c6a65d40da9b6b9e8a08d9731e
出典データセット
uspto-grants-2016_06
特許番号
US09365506B2

反応ノート

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