Diethyl Ether → HCID 54254937, compound

HRID 1757075Notes

Reaction equation

HRID 1757075 reaction equation
[C@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2C2C=C(CCO)C=CC=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3].CC(OI1(OC(C)=O)(OC(C)=O)O[C:39](=O)[C:38]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]1=2)=O.C[CH2:51][O:52]CC>ClCCl>[C@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:37]2[CH:36]=[CH:35][CH:34]=[CH:33][C:38]=2[CH2:39][CH:51]=[O:52])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 54271958HCID 54271958, compound

Product 1

HCID 54254937HCID 54254937, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(3-(2-α-D-mannopyranosyloxyphenyl)phenyl)ethanol (1.12 g, 2.46 mmol) in dichloromethane (15 ml) was added slowly to a suspension of Dess-Martin periodinane (4.95 g, 11.7 mmol) in dry dichloromethane (5 ml), and the reaction was stirred at room temperature overnight. The mixture was then diluted with ether and filtered; the filtrate was washed twice with saturated sodium bicarbonate solution and once with brine, then dried with magnesium sulfate. The solvent was removed in vacuo and the residue was purified by silica gel chromatography (4:1 hexane:ethyl acetate) to afford 2-(2-α-D-mannopyranosyloxyphenyl)phenylethanal (0.63 g, 57%).

Workup

  1. filtrationfiltered
  2. washthe filtrate was washed twice with saturated sodium bicarbonate solution and once with brine
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by silica gel chromatography (4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-13e1d0d7b2d84734b65cdc365dea1261
Source dataset
uspto-grants-1995_08
Patent number
US05444050

Reaction notes

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