Sodium methanolate methanol → HCID 86658286, compound

HRID 74849Notes

Reaction equation

HRID 74849 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C@@H:25]1[C@@H:65]([CH2:66][O:67]C(=O)C)[O:64][C@@H:28]([O:29][N:30]2[CH:34]=[C:33]([CH2:35][O:36][C@H:37]3[CH2:61][CH2:60][C@@:59]4([CH3:62])[CH:39]([CH2:40][CH2:41][C@@H:42]5[C@@H:58]4[CH2:57][CH2:56][C@@:55]4([CH3:63])[C@H:43]5[CH2:44][CH2:45][C@@H:46]4[C@H:47]([CH3:54])[CH2:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH2:38]3)[N:32]=[N:31]2)[C@H:27]([O:71]C(=O)C)[C@H:26]1[O:75]C(=O)C)(=O)C.C[O-].[Na+].CO>CO.C(Cl)(Cl)Cl.CO>[C@@H:6]1([O:24][C@@H:25]2[C@@H:65]([CH2:66][OH:67])[O:64][C@@H:28]([O:29][N:30]3[CH:34]=[C:33]([CH2:35][O:36][C@H:37]4[CH2:61][CH2:60][C@@:59]5([CH3:62])[CH:39]([CH2:40][CH2:41][C@@H:42]6[C@@H:58]5[CH2:57][CH2:56][C@@:55]5([CH3:63])[C@H:43]6[CH2:44][CH2:45][C@@H:46]5[C@H:47]([CH3:54])[CH2:48][CH2:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH2:38]4)[N:32]=[N:31]3)[C@H:27]([OH:71])[C@H:26]2[OH:75])[O:7][C@H:8]([CH2:19][OH:20])[C@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

5

Reactant 2

HCID 23694274Sodium methanolate methanol2×HCID 866582874-(Cholestan-3beta-yl-oxymethyl)[1,2,3]triazol-1-yl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside

Product 1

HCID 86658286HCID 86658286, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 21584188Chloroform methanolSolvent

Procedure

Dry N-glycoside 91 (100 mg, 0.092 mmol) was dissolved in anhydrous CH3OH and a solution of NaOMe/CH3OH (11M, 30 μL) was added dropwise to the mixture at 0° C. under argon. The solution was allowed to stir at RT overnight. After monitoring by TLC, additional anhydrous CH3OH (2 mL) and NaOMe/CH3OH (11M, 50 μL) was added and the reaction mixture found to be pH 11. Upon completion, the reaction was neutralised to pH 6 by the addition of Dowex H+ ion-exchange resin, and the resulting suspension dissolved in CHCl3/CH3OH (1:1) at 40° C. The solution was filtered, concentrated and dried over P2O5 to yield the crude product.

Workup

  1. additionwas added
  2. additionUpon completion, the reaction was neutralised to pH 6 by the addition of Dowex H+ ion-exchange resin
  3. filtrationThe solution was filtered
  4. concentrationconcentrated
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-628078b4457d44d2b5c4780004a6c8d0
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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