HCID 131736866, compound → HCID 131736865, compound

HRID 1488270Notes

Reaction equation

HRID 1488270 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:50]([O:51][CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@@H:49]([CH2:59][O:60][C@H:61]2[O:93][C@H:92]([CH2:94][O:95]C(=O)C3C=CC=CC=3)[C@@H:82]([O:83]C(=O)C3C=CC=CC=3)[C@H:72]([O:73]C(=O)C3C=CC=CC=3)[C@@H:62]2[O:63]C(=O)C2C=CC=CC=2)[O:48][C@@H:47]([O:104][CH2:105][CH2:106][NH:107][C:108](=[O:117])[O:109][CH2:110][C:111]2[CH:116]=[CH:115][CH:114]=[CH:113][CH:112]=2)[C@@H:46]1[O:118]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O(C)[Na]>CO>[C@H:11]1([O:44][C@H:45]2[C@H:50]([O:51][CH2:52][C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)[C@@H:49]([CH2:59][O:60][C@H:61]3[O:93][C@H:92]([CH2:94][OH:95])[C@@H:82]([OH:83])[C@H:72]([OH:73])[C@@H:62]3[OH:63])[O:48][C@@H:47]([O:104][CH2:105][CH2:106][NH:107][C:108](=[O:117])[O:109][CH2:110][C:111]3[CH:112]=[CH:113][CH:114]=[CH:115][CH:116]=3)[C@@H:46]2[OH:118])[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 131736866HCID 131736866, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 131736865HCID 131736865, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of benzyl (2-{[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→3)-[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→6)]-2-O-benzoyl-4-O-benzyl-β-D-glucopyranosyl]oxy}ethyl)carbamate (3.39 g, 1.984 mmol) in CH3OH (30 mL) was added NaOCH3 (0.4 mL, 0.2 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. The resulting mixture was allowed to stir for additional 15 min. The resin was filtered off and washed with CH3OH (3×5 mL). The filtrate was concentrated to give the title compound. UPLC Method B: calculated for C35H49NO18 771.29, observed m/e: 772.42 [M+1]; Rt=2.51 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. stirringto stir for additional 15 min
  4. filtrationThe resin was filtered off
  5. washwashed with CH3OH (3×5 mL)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d1b82cf3590b4ec68106749117ecce04
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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