methyl alpha-D-glucopyranoside → HCID 22819440, 화합물

HRID 1447499

반응식

HRID 1447499 반응식
[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:25])=[CH:15]/[C:16]3[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[O:27]([CH3:39])[C@H:28]1[O:36][C@H:35]([CH2:37][OH:38])[C@@H:33]([OH:34])[C@H:31]([OH:32])[C@H:29]1[OH:30]>CCOCC.N1C=CC=CC=1>[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:25])=[CH:15]/[C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:30][C@@H:29]4[C@@H:31]([OH:32])[C@H:33]([OH:34])[C@@H:35]([CH2:37][O:38][C:20](=[O:21])[C:19]5[CH:23]=[CH:24][C:16](/[CH:15]=[C:14](/[C:6]6[CH:5]=[CH:4][C:3]7[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=7[CH:7]=6)\[CH3:25])=[CH:17][CH:18]=5)[O:36][C@@H:28]4[O:27][CH3:39])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2.[CH3:1][C:2]1([CH3:26])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6](/[C:14](/[CH3:25])=[CH:15]/[C:16]3[CH:24]=[CH:23][C:19]([C:20]([O:32][C@H:31]4[C@H:33]([OH:34])[C@@H:35]([CH2:37][O:38][C:20](=[O:21])[C:19]5[CH:23]=[CH:24][C:16](/[CH:15]=[C:14](/[C:6]6[CH:5]=[CH:4][C:3]7[C:2]([CH3:26])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=7[CH:7]=6)\[CH3:25])=[CH:17][CH:18]=5)[O:36][C@H:28]([O:27][CH3:39])[C@@H:29]4[OH:30])=[O:21])=[CH:18][CH:17]=3)[CH:5]=[CH:4][C:3]1=2

참가 물질

6

반응물 2

HCID 64947methyl alpha-D-glucopyranosideHCID 12836534HCID 12836534, 화합물

생성물 2

HCID 22819440HCID 22819440, 화합물HCID 70523303HCID 70523303, 화합물

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

A solution of 100 mmol of p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl chloride in 450 ml of ether was added while stirring at 0° C. over a period of 1 hour to a solution of 19.5 g of methyl α-D-glucopyranoside in 500 ml of pyridine. The mixture was stirred at 0° C. for a further 4 hours and at room temperature for 16 hours and then evaporated to dryness. The residue was dissolved in ethyl acetate and the extract was washed with 3 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and water. After drying over sodium sulphate, the organic phase was evaporated and the residue was chromatographed on silica gel (hexane/ethyl acetate) to give methyl 2,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranoside, melting point 203°-204° C. (from ethyl acetate), [α]D25 =+27.4° (c=1 in chloroform), and methyl 3,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-α-D-glucopyranoside, melting point 128°-129° C. (with decomposition, from methanol), [α]D25 =+135° (c=1 in chloroform).

후처리

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe extract was washed with 3 N hydrochloric acid, water, saturated aqueous sodium bicarbonate solution and water
  4. dry with materialAfter drying over sodium sulphate
  5. customthe organic phase was evaporated
  6. customthe residue was chromatographed on silica gel (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-790f5b17a8354b518b477bd53a9b33d1
출처 데이터셋
uspto-grants-1982_02
특허 번호
US04316983

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