HCID 131736869, compound → HCID 131736868, compound

HRID 1488275Notes

Reaction equation

HRID 1488275 reaction equation
C([O:9][C@H:10]1[C@@H:15]([O:16]C(=O)C2C=CC=CC=2)[C@H:14]([O:25]C(=O)C2C=CC=CC=2)[C@@H:13]([CH2:34][O:35]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[O:44][C@H:45]1[C@H:56]([O:57][CH2:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C@@H:55]([CH2:65][O:66][C@H:67]2[O:99][C@H:98]([CH2:100][O:101]C(=O)C3C=CC=CC=3)[C@@H:88]([O:89]C(=O)C3C=CC=CC=3)[C@H:78]([O:79]C(=O)C3C=CC=CC=3)[C@@H:68]2[O:69]C(=O)C2C=CC=CC=2)[O:54][C@@H:47]([O:48][CH2:49][CH2:50][N:51]=[N+:52]=[N-:53])[C@@H:46]1[F:110])(=O)C1C=CC=CC=1.O(C)[Na]>CO>[C@H:11]1([O:44][C@H:45]2[C@H:56]([O:57][CH2:58][C:59]3[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=3)[C@@H:55]([CH2:65][O:66][C@H:67]3[O:99][C@H:98]([CH2:100][OH:101])[C@@H:88]([OH:89])[C@H:78]([OH:79])[C@@H:68]3[OH:69])[O:54][C@@H:47]([O:48][CH2:49][CH2:50][N:51]=[N+:52]=[N-:53])[C@@H:46]2[F:110])[O:12][C@H:13]([CH2:34][OH:35])[C@@H:14]([OH:25])[C@H:15]([OH:16])[C@@H:10]1[OH:9]

Participants

4

Reactant 2

HCID 131736869HCID 131736869, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 131736868HCID 131736868, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-azidoethyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→6)]-4-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranoside (5.0 g, 3.34 mmol) in CH3OH (40 mL) was added NaOCH3 (1.0 mL, 0.5 mmol, 0.5 M in CH3OH). After stirring at rt for 24 hr, amberlite IR 120 (H) ion exchange resin (pre-washed with CH3OH 3×30 mL) was added to the reaction mixture. After 15 min, the resin was filtered off and washed with CH3OH (3×5 mL). The filtrate was concentrated and the residue was taking into EtOAc (50 mL) and stirred for 2 hr. The solid was filtered, and washed with EtOAc (3×15 mL) and dried to give the title compound. UPLC Method B: calculated for C27H40FN3O15 665.24, observed m/e: 666.35 [M+1]; Rt=2.03 min.

Workup

  1. washamberlite IR 120 (H) ion exchange resin (pre-washed with CH3OH 3×30 mL)
  2. additionwas added to the reaction mixture
  3. waitAfter 15 min
  4. filtrationthe resin was filtered off
  5. washwashed with CH3OH (3×5 mL)
  6. concentrationThe filtrate was concentrated
  7. stirringstirred for 2 hr
  8. filtrationThe solid was filtered
  9. washwashed with EtOAc (3×15 mL)
  10. customdried

Sources & evidence

ORD record
ord-b366a2b9481b49a4aaa5f8229047064f
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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