3,4-dihydro-2H-pyran → benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate

HRID 2106845

反応式

[CH2:1]([C@@H:7]([C@@H:18]([O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:19][C@H:20]([OH:32])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[O:41]1[CH:46]=[CH:45][CH2:44][CH2:43][CH2:42]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl>[CH2:1]([C@@H:7]([C@@H:18]([O:33][Si:34]([C:37]([CH3:38])([CH3:39])[CH3:40])([CH3:36])[CH3:35])[CH2:19][C@H:20]([O:32][CH:42]1[CH2:43][CH2:44][CH2:45][CH2:46][O:41]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:8]([O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

参加物

反応条件

温度: -15 °C

実験手順

(M)(f) 350 mg of benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)oxy]-5-hydroxyhexadecanoate and 0.5 ml of freshly distilled 3,4-dihydro-2H-pyran were dissolved in 10 ml of methylene chloride and cooled to -15° C. A crystal of p-toluenesulfonic acid monohydrate was added thereto. The mixture was stirred until the reaction has finished. Thereupon, the solution was evaporated and the residue was chromatographed on silica gel. There were obtained 330 mg of benzyl (2S,3S,5R)-2-hexyl-3-[(t-butyldimethylsilyl)-oxy]-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoate, MS: 603 (M+ -t-butyl).

後処理

customThereupon, the solution was evaporated
customthe residue was chromatographed on silica gel

出典と根拠

ORDレコード: ord-023f51e0e3464a3fb8721e961bd4c281
出典データセット: uspto-grants-1990_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04931463

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 1

反応条件

実験手順

後処理

出典と根拠

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