Methyl iodide → HCID 54129607, compound

HRID 2399556Notes

Reaction equation

HRID 2399556 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([OH:17])[C@H:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][O:13][C@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:28]I>CN(C=O)C>[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH3:28])[C@H:15]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][O:13][C@H:10]1[O:11][CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 53782419HCID 53782419, compound

Product 1

HCID 54129607HCID 54129607, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2,4-di-O-benzyl-b-D-xylopyranoside (38 g, 0.11 mole) in dry DMF (500 ml) was added 60% NaH in oil (4.4 g, 0.11 mole). After stirring at 0° C. for 30 min, methyl iodide (17 g, 0.12 mole) was added and the reaction mixture was allowed to warm to room temperature. The solution was continued to stir for 1 hr and evaporated to dryness under reduced pressure. The oily residue was partitioned between ether (300 ml) and water (300 ml). The ether layer was dried over anhydrous sodium sulfate, evaporated to dryness under reduced pressure to give methyl 2,4-di-O-benzyl-3-O-methyl-b-D-xylopyranoside (39.4 g, 100% yield) as colorless oil; EI-MS: m/z 358 (M+), 254 (M+ -Bn); 1H-NMR (CDCl3)d: 3.18 (1H,dd,J=10 & 12 Hz), 3.24 (1H,dd, J=7.5 & 9 Hz), 3.29 (1H,t,J=9 Hz), 3.50 (1H,m), 3.52 (3H, s), 3.65 (3H,s), 3.9 (1H,dd,J=5.9 & 12 Hz), 4.21 (1H,d,J=7.5 Hz), 4.62 (1H,d,J=12 Hz), 4.69 (1H,d,J=11 Hz), 4.75 (1H,d,J=12 Hz), 4.85 (1H,d,11 Hz), 7.35 (10 br.s).

Workup

  1. temperatureto warm to room temperature
  2. stirringto stir for 1 hr
  3. customevaporated to dryness under reduced pressure
  4. customThe oily residue was partitioned between ether (300 ml) and water (300 ml)
  5. dry with materialThe ether layer was dried over anhydrous sodium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d21074b09ffa4599bf1e9567f0f4f3a6
Source dataset
uspto-grants-1995_09
Patent number
US05449785

Reaction notes

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