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Imidazole → (3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

HRID 355204
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HRID 355204 반응식
[C:1]([O:9][C@@H:10]1[CH2:17][C@H:16]2[C@H:12]([CH2:13][C:14](=[O:18])[O:15]2)[C@H:11]1[CH2:19][OH:20])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:26]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])([CH3:28])[CH3:27].S(=O)(=O)(O)O>CN(C)C=O.CCOCC.[Cl-].[Na+].O>[C:1]([O:9][C@@H:10]1[CH2:17][C@H:16]2[C@H:12]([CH2:13][C:14](=[O:18])[O:15]2)[C@H:11]1[CH2:19][O:20][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:32])[CH3:31])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

8

반응물 4

HCID 795ImidazoleHCID 1118Sulfuric AcidHCID 28928tert-Butyldimethylsilyl chlorideHCID 2724454(3aR,4S,5R,6aS)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one

생성물 1

HCID 2724503(3aR,4S,5R,6aS)-4-(((tert-Butyldimethylsilyl)oxy)methyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl benzoate

시약·촉매·용매 3

HCID 3283Diethyl Ether용매
HCID 6228Dimethylformamide용매
HCID 57417360Sodium chloride; water용매

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온도
20 °C

실험 절차

A solution of 16.58 g of (1S,5R,6S,7R)-7-benzoyloxy-6-hydroxymethyl-2-oxabicyclo[3.3.0]octan-3-one in 18 ml of dimethylformamide is combined at 0° C. with 10.21 g of imidazole and 10.85 g of tert.-butyldimethylsilyl chloride. The mixture is stirred for 24 hours at 20° C., diluted with 1.5 l of ether, shaken in succession with 5% sulfuric acid and brine, dried over magnesium sulfate, and evaporated under vacuum. The residue is recrystallized from hexane.

후처리

  1. dry with materialdried over magnesium sulfate
  2. customevaporated under vacuum
  3. customThe residue is recrystallized from hexane

출처 및 근거

ORD 기록
ord-f6afcd1fcd7a4609b4668316af90c450
출처 데이터셋
uspto-grants-1983_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04378370

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