methyl alpha-D-glucopyranoside → HCID 22819440、化合物

HRID 1447499ノート

反応式

HRID 1447499 の反応式
[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

参加物

6

反応物 2

HCID 64947methyl alpha-D-glucopyranosideHCID 12836534HCID 12836534、化合物

生成物 2

HCID 22819440HCID 22819440、化合物HCID 70523303methyl 2,6-bis-O-[p-[(E)-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-propenyl]-benzoyl]-alpha-D-glucopyranoside

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-790f5b17a8354b518b477bd53a9b33d1
出典データセット
uspto-grants-1982_02
特許番号
US04316983

反応ノート

読み込み中…