methyl alpha-D-glucopyranoside → HCID 22819440, compound

HRID 1447499Notes

Reaction equation

HRID 1447499 reaction equation
[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

Participants

6

Reactant 2

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

Product 2

HCID 22819440HCID 22819440, compoundHCID 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

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-790f5b17a8354b518b477bd53a9b33d1
Source dataset
uspto-grants-1982_02
Patent number
US04316983

Reaction notes

Loading…