HCID 86751606, compound → HCID 86751605, compound

HRID 2293881Notes

Reaction equation

HRID 2293881 reaction equation
[N:1]([C@H:4]([C@H:50]([O:66][C:67](=[O:74])[C:68]1[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=1)/[CH:51]=[CH:52]/[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[CH2:5][O:6][C@H:7]1[O:39][C@H:38]([CH2:40][O:41][CH2:42][C:43]([O:45]C(C)(C)C)=[O:44])[C@H:28]([O:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[C@H:18]([O:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:8]1[O:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N+:2]=[N-:3]>FC(F)(F)C(O)=O>[C:67]([O:66][C@H:50](/[CH:51]=[CH:52]/[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH3:65])[C@@H:4]([N:1]=[N+:2]=[N-:3])[CH2:5][O:6][C@H:7]1[O:39][C@H:38]([CH2:40][O:41][CH2:42][C:43]([OH:45])=[O:44])[C@H:28]([O:29][CH2:30][C:31]([OH:33])=[O:32])[C@H:18]([O:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:8]1[O:9][C:10](=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:74])[C:68]1[CH:69]=[CH:70][CH:71]=[CH:72][CH:73]=1

Participants

3

Reactant 1

HCID 86751606HCID 86751606, compound

Product 1

HCID 86751605HCID 86751605, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
22 °C

Procedure

A solution of (2S,3R,4E)-2-Azido-3-benzoyloxy-1-(2,3-di-O-benzoyl-4,6-di-O-tert-butyloxycarbonylmethyl-α-D-galactopyranosyloxy)-4-octadecene described in Example 1-F (0.145 g, 0.14 mmol) in aqueous trifluoroacetic acid (90%, 3 mL) was stirred at 22° C. during 5 minutes. The solvents were evaporated under vacuum and the residue was co-evaporated with toluene (3×5 mL) and then dissolved in a mixture of dioxane/water (1:1, 10 mL). This mixture was stirred at 22° C. for 30 minutes. The solvents were evaporated under vacuum and the residue was co-evaporated again with toluene (4×10 mL). The residue was purified by silica gel plates (chloroform/methanol/water 75:25:2). The residue upon solvent evaporation was redissolved in methylene chloride/methanol (1:1, 40 mL) and treated at 0° C. (ice bath) with Dowex 50W X8 (H+) resin for 40 minutes to give the title compound (0.076 g, 59%).

Workup

  1. customThe solvents were evaporated under vacuum
  2. dissolutiondissolved in a mixture of dioxane/water (1:1, 10 mL)
  3. stirringThis mixture was stirred at 22° C. for 30 minutes
  4. customThe solvents were evaporated under vacuum
  5. customThe residue was purified by silica gel plates (chloroform/methanol/water 75:25:2)
  6. customThe residue upon solvent evaporation
  7. dissolutionwas redissolved in methylene chloride/methanol (1:1, 40 mL)
  8. additiontreated at 0° C. (ice bath) with Dowex 50W X8 (H+) resin for 40 minutes

Sources & evidence

ORD record
ord-7beadccf5c484522aab1cf2fbc12b4f7
Source dataset
uspto-grants-1997_11
Patent number
US05686426

Reaction notes

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