Benzyl Alcohol → Benzyl 2,3,4-tri-O-acetyl-alpha-D-lyxopyranoside

HRID 964863Notes

Reaction equation

HRID 964863 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@@H:6]1Br)(=[O:3])[CH3:2].[CH2:20]([OH:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Hg]C#N>C(#N)C.[Hg]Br>[C:1]([O:4][C@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[CH2:8][O:7][C@@H:6]1[O:27][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 244Benzyl AlcoholHCID 130488932,3,4-tri-O-acetyl-alpha-lyxopyranosyl bromideHCID 14367217Cyanide mercury

Product 1

HCID 67638320Benzyl 2,3,4-tri-O-acetyl-alpha-D-lyxopyranosideYield 96.1%

Reagents, catalysts & solvents 2

HCID 24830Mercury bromideCatalystHCID 6342AcetonitrileSolvent

Procedure

A solution of compound 2 (21 g, 61.9 mmol) in acetonitrile (200 ml) and benzyl alcohol (9.6 ml, 92.3 mmol) was vigorously stirred with molecular sieves (4 Å, 25 g), mercury bromide (25 g, 69.4 mmol), mercury cyanide (18.2 g, 12.0 mmol) under argon for 18 hours. The organic layer was filtered through celite and diluted with dichloromethane (250 ml) which was washed with water, aq. NaHCO3 and aq. NaCl and dried (Na2 SO4). The solvent was filtered and then evaporated under reduced pressure. The syrupy residue was chromatographed on silica gel (filter technique) using 1.5:1 hexane-ethyl acetate to give 3 (21.8 g, 90.0%).

Workup

  1. filtrationThe organic layer was filtered through celite
  2. additiondiluted with dichloromethane (250 ml) which
  3. washwas washed with water, aq. NaHCO3 and aq. NaCl
  4. customdried (Na2 SO4)
  5. filtrationThe solvent was filtered
  6. customevaporated under reduced pressure
  7. customThe syrupy residue was chromatographed on silica gel (filter technique)

Sources & evidence

ORD record
ord-d563b2c918d148debb74d76c47142d92
Source dataset
uspto-grants-1998_06
Patent number
US05773239

Reaction notes

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