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Water → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4- hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

HRID 1474602
ノート
印刷プレビュー

反応式

HRID 1474602 の反応式
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@:6]1([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([O:40][Si](C(C)(C)C)(C)C)=[CH:36][CH:35]=2)[CH:27]=1)OC)(=[O:3])[CH3:2].O.C([SiH](CC)CC)C.C(OC(=O)C)C>C(#N)C>[C:16]([O:15][C@H:9]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([CH2:33][C:34]3[CH:35]=[CH:36][C:37]([OH:40])=[CH:38][CH:39]=3)[CH:27]=2)[O:7][C@@H:8]1[CH2:19][O:20][C:21](=[O:23])[CH3:22])(=[O:18])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12052Triethylsilane2 回HCID 71118346HCID 71118346、化合物

生成物 1

HCID 67115824(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4- hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate収率 86.27%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

To a solution of (2S,3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl triacetate (44.0 g, 0.064 mol) in acetonitrile (200 mL), water (1.15 mL, 0.064 mol), triethylsilane (32.45 mL, 0.203 mol) and borontrifluoroetherate (15.94 mL, 0.127 mol) were added at 10° C. The resulting mixture was stirred at r.t. for 16 h. Additional amounts of triethylsilane (3.25 mL, 0.020 mol) and borontrifluoroetherate (1.59 mL, 0.013 mol) were added at 10° C. and heated at 30° C. for 6 h. Ethylacetate (1 L) was added to the reaction mixture, washed it with saturated NaHCO3 solution (2×500 mL), water (500 mL) and brine (500 mL) successively. The organic layer was dried over anhydrous Na2SO4 and volatiles were evaporated in vacuo. The residue obtained was purified by column chromatography (silica gel, 4:6 Ethyl acetate:Pet.Ether) to provide title compound (30 g, 86.27%) as off-white solid.

後処理

  1. temperatureheated at 30° C. for 6 h
  2. washwashed it with saturated NaHCO3 solution (2×500 mL), water (500 mL) and brine (500 mL) successively
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4 and volatiles
  4. customwere evaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by column chromatography (silica gel, 4:6 Ethyl acetate:Pet.Ether)

出典と根拠

ORDレコード
ord-4ac06fd060ac46b7b4980ed678a5358f
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09018249B2

反応ノート

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