delta-Gluconolactone → (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

HRID 46186

反応式

HRID 46186 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH:19]=1)[CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11].[CH2:21]([Li])[CH2:22][CH2:23][CH3:24].[CH2:26]([OH:37])[C@H:27]1[O:33][C:31](=[O:32])[C@H:30]([OH:34])[C@@H:29]([OH:35])[C@@H:28]1[OH:36]>O1CCCC1>[CH2:21]([O:34][C@@H:30]1[C@@H:29]([O:35][CH2:21][C:22]2[CH:11]=[CH:10][CH:12]=[CH:24][CH:23]=2)[C@H:28]([O:36][CH2:21][C:22]2[CH:14]=[CH:13][CH:15]=[CH:24][CH:23]=2)[C@@H:27]([CH2:26][O:37][CH2:7][C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][CH:19]=2)[O:33][C:31]1([C:2]1[CH:3]=[CH:4][C:5]([Cl:20])=[C:6]([CH2:7][O:8][Si:9]([CH:16]([CH3:18])[CH3:17])([CH:13]([CH3:15])[CH3:14])[CH:10]([CH3:12])[CH3:11])[CH:19]=1)[OH:32])[C:22]1[CH:18]=[CH:16][CH:17]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 7027delta-Gluconolactone2 回HCID 67153939(5-Bromo-2-chlorobenzyloxy)triisopropylsilane2 回HCID 178418339Butyllithium

生成物 1

HCID 67287055(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)-tetrahydro-2H-pyran-2-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (5-Bromo-2-chlorobenzyloxy)triisopropylsilane (compound 4, 97 g, 257 mmol) from Step 3 in tetrahydrofuran (1 L) at −78° C. under an atmosphere of nitrogen was added dropwise n-butyllithium (2.5 M in hexanes, 103 mL, 257 mmol), and the mixture was stirred for 1.5 h at the same temperature. Then a solution of 2,3,4,6-tetra-O-benzyl-D-glucopyranone (compound 2, 106 g, 198 mmol) from Step 1 in tetrahydrofuran (500 mL) was added dropwise, and the mixture was stirred for 3 h at the same temperature. The reaction mixture was quenched by addition of saturated ammonium chloride solution. After complete addition, the solution was gradually raised to room temperature. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a yellow oil which was used without further purification.

後処理

  1. stirringthe mixture was stirred for 3 h at the same temperature
  2. customThe reaction mixture was quenched by addition of saturated ammonium chloride solution
  3. additionAfter complete addition
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-a780a61119ba441c9529ed88dfc75f77
出典データセット
uspto-grants-2013_09
特許番号
US08541380B2

関連ノート

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