Methanol → Methyl 2-deoxy-5-O-(triphenylmethyl)-D-erythro-pentofuranoside

HRID 1199117Notes

Reaction equation

HRID 1199117 reaction equation
[O:1]([CH3:10])[CH:2]1[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[CH2:3]1.[C:11]1([C:17](Cl)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CO>N1C=CC=CC=1>[C:17]([O:9][CH2:8][C@H:6]1[O:7][CH:2]([O:1][CH3:10])[CH2:3][C@@H:4]1[OH:5])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6456Trityl chlorideHCID 10154128Methyl 2-deoxy-D-erythro-pentofuranoside

Product 1

HCID 13912247Methyl 2-deoxy-5-O-(triphenylmethyl)-D-erythro-pentofuranoside

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 11.2 g (0.07 mole) of methyl 2-deoxyribofuranoside (90% pure) in 60 ml of dry pyridine under a dry nitrogen atmosphere were added 19.0 g (0.07 mole) of triphenylmethyl chloride. The mixture was stirred at ambient temperature for three days. Methanol (35 ml) was then added. The solvents were then evaporated under reduced pressure. The residue was taken up in 200 ml of ethyl acetate, washed with 75 ml of 5% sodium bicarbonate followed by a 75 ml wash with DI (deionized) water. The organic layer was dried (Na2SO4), filtered and the solvent removed under vacuum affording a sticky, viscous oil. This crude methyl 2-deoxy-5-O-tritylriboruanoside compound was used without further purification in subsequent synthetic procedures.

Workup

  1. customThe solvents were then evaporated under reduced pressure
  2. washwashed with 75 ml of 5% sodium bicarbonate
  3. washwash with DI (deionized) water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent removed under vacuum
  7. customaffording a sticky, viscous oil
  8. customThis crude methyl 2-deoxy-5-O-tritylriboruanoside compound was used without further purification in subsequent synthetic procedures

Sources & evidence

ORD record
ord-ceaee069a7f34363861c0da5be98141e
Source dataset
uspto-grants-1990_02
Patent number
US04898936

Reaction notes

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