Hydrogen Bromide → 1,3,5-tri-O-benzoyl-alpha-L-ribofuranose

HRID 865635Notes

Reaction equation

HRID 865635 reaction equation
[C:1]([O:4][C@H:5]1[O:27][C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:6]1[O:7]C(=O)C1C=CC=CC=1)(=[O:3])C.Br.O>C(Cl)Cl>[C:1]([O:4][C@@H:5]1[O:27][C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:6]1[OH:7])(=[O:3])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 110488431,3,5-tri-O-benzoyl-alpha-L-ribofuranose

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Compound 10 (9 g, 17.84 mmol) was stirred in 100 ml of CH2Cl2 at 0° C. while 70 ml of CH2Cl2 containing HBr (3.2 g, 30.5 mmol) was added in one portion. The mixture was stirred at 0° C. for 3.5 hrs, water (55 ml) was added and the mixture stirred at r.t. for 18 hrs. The organic layer was separated, washed with sat. NaHCO3, dried (MgSO4). After evaporation of the solvent, a foam was obtained, which upon recrystallization from CH2Cl2 and n-hexane, gave 11 as a white solid. (6.2 g, 75.5%). m.p. 137°-138° C., lit. 140°-141° C., [α]D =-81.960 (c 0.55, CHCl3 ; D form: [α]D =+83.71.

Workup

  1. additionwas added in one portion
  2. stirringthe mixture stirred at r.t. for 18 hrs
  3. customThe organic layer was separated
  4. washwashed with sat. NaHCO3
  5. dry with materialdried (MgSO4)
  6. customAfter evaporation of the solvent
  7. customa foam was obtained
  8. customwhich upon recrystallization from CH2Cl2 and n-hexane

Sources & evidence

ORD record
ord-573ee56e06e947699ef64d94373d05f7
Source dataset
uspto-grants-1996_10
Patent number
US05567688

Reaction notes

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