Sodium Methoxide → HCID 131736873, compound

HRID 1488299Notes

Reaction equation

HRID 1488299 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[CH2:44][CH:45]([NH:93][C:94](=[O:103])[O:95][CH2:96][C:97]1[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=1)[CH2:46][C:47]([OH:92])([OH:91])[C@H:48]1[O:80][C@H:79]([CH2:81][O:82]C(=O)C2C=CC=CC=2)[C@@H:69]([O:70]C(=O)C2C=CC=CC=2)[C@H:59]([O:60]C(=O)C2C=CC=CC=2)[C@@H:49]1[O:50]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[C@H:11]1([CH2:44][CH:45]([NH:93][C:94](=[O:103])[O:95][CH2:96][C:97]2[CH:102]=[CH:101][CH:100]=[CH:99][CH:98]=2)[CH2:46][C:47]([OH:91])([OH:92])[C@H:48]2[O:80][C@H:79]([CH2:81][OH:82])[C@@H:69]([OH:70])[C@H:59]([OH:60])[C@@H:49]2[OH:50])[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 10942334Sodium MethoxideHCID 131736874HCID 131736874, compound

Product 1

HCID 131736873HCID 131736873, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of Benzyl (1[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl],4[2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl]-dihydroxybutan-2-yl)carbamate (9.72 g, 6.96 mmol) in Methanol (30 mL) was added 0.5M sodium methoxide (1.5 mL, 0.750 mmol) in methanol. After stirring at room temperature for 48 hour, amberlite IR 120 (H) ion exchange resin (pre-washed with methanol 3×30 ml) was added to reaction mixture, and allowed stirring for additional 15 minutes. The ion exchange resin was filtered off and washed with methanol (2×5 mL). The filtrate was concentrated down and the residue was purified on 86 g C18 column reverse phase, eluting with 5% CH3CN in water (3 cv) then 5% to 50% CH3CN in water (20 cv) to give the title compound as a white solid. UPLC-MS: calculated for C24H37NO14 563.22 observed m/e: 564.24 (M+H)+(Rt: 2.31/5.00 min).

Workup

  1. washamberlite IR 120 (H) ion exchange resin (pre-washed with methanol 3×30 ml)
  2. additionwas added to reaction mixture
  3. stirringallowed stirring for additional 15 minutes
  4. filtrationThe ion exchange resin was filtered off
  5. washwashed with methanol (2×5 mL)
  6. concentrationThe filtrate was concentrated down
  7. customthe residue was purified on 86 g C18 column reverse phase
  8. washeluting with 5% CH3CN in water (3 cv)

Sources & evidence

ORD record
ord-e90a0da8ca474c7085115bd002706aa2
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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