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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
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HRID 1474602 반응식
[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]
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참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 12052Triethylsilane2회HCID 71118346HCID 71118346, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4ac06fd060ac46b7b4980ed678a5358f
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09018249B2

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