Imidazole → HCID 15677365, compound

HRID 858168Notes

Reaction equation

HRID 858168 reaction equation
[CH2:1]([S:8][CH:9]([S:39]CC1C=CC=CC=1)[C@H:10]([C@@H:19]([C@@H:28]([CH2:30][O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)O)[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[O:11]CC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.N1C=CN=C1.[C:73]1([CH3:79])[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1.C(#N)C>>[CH2:79]([O:11][C@H:10]1[C@H:19]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:28]([CH2:30][O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[S:39][CH:9]1[S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1

Participants

6

Reactant 5

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 21584213Acetonitrile tolueneHCID 86598645HCID 86598645, compound

Product 1

HCID 15677365HCID 15677365, compound

Conditions

Temperature
90 °C

Procedure

To a solution of 4 (13.0 g, 20 mmol) in dry 2:1 toluene/acetonitrile (200 mL) were added triphenylphosphine (15.7 g, 60 mmol), iodine (12.7 g, 50 mmol) and imidazole (5.44 g, 80 mmol). The reaction mixture was stirred at 90° C. for 24 hours after which time the solution was evaporated to dryness. The crude product was purified by silica gel chromatography (cyclohexane/EtOAc, 4:1) to afford benzyl 2,3,5-tri-O-benzyl-1,4-dithio-L-Xylofuranoside as a syrup (5, 9.0 g, 72%). MS 543 (M+H)+.

Workup

  1. customwas evaporated to dryness
  2. customThe crude product was purified by silica gel chromatography (cyclohexane/EtOAc, 4:1)

Sources & evidence

ORD record
ord-440262cf9d6e4366af39dd74fe36ca5d
Source dataset
uspto-grants-2006_12
Patent number
US07148223B2

Reaction notes

Loading…