Sodium Methoxide → HCID 86658283, compound

HRID 74843

Reaction equation

HRID 74843 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]C(=O)C2C=CC=CC=2)[C@@H:49]([CH2:60][O:61]C(=O)C2C=CC=CC=2)[O:48][C@H:47]([O:70][C@H:71]2[C@H:114]([O:115]C(=O)C3C=CC=CC=3)[C@@H:113]([CH2:124][O:125]C(=O)C3C=CC=CC=3)[O:112][C@H:73]([O:74][CH2:75][CH2:76][CH2:77][N:78]3[CH:82]=[C:81]([CH2:83][O:84][C@H:85]4[CH2:109][CH2:108][C@@:107]5([CH3:110])[CH:87]([CH2:88][CH2:89][C@@H:90]6[C@@H:106]5[CH2:105][CH2:104][C@@:103]5([CH3:111])[C@H:91]6[CH2:92][CH2:93][C@@H:94]5[C@H:95]([CH3:102])[CH2:96][CH2:97][CH2:98][CH:99]([CH3:101])[CH3:100])[CH2:86]4)[N:80]=[N:79]3)[C@H:72]2[O:134]C(=O)C2C=CC=CC=2)[C@H:46]1[O:143]C(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>C1COCC1.CO>[C@H:11]1([O:44][C@H:45]2[C@H:50]([OH:51])[C@@H:49]([CH2:60][OH:61])[O:48][C@H:47]([O:70][C@H:71]3[C@H:114]([OH:115])[C@@H:113]([CH2:124][OH:125])[O:112][C@H:73]([O:74][CH2:75][CH2:76][CH2:77][N:78]4[CH:82]=[C:81]([CH2:83][O:84][C@H:85]5[CH2:109][CH2:108][C@@:107]6([CH3:110])[CH:87]([CH2:88][CH2:89][C@@H:90]7[C@@H:106]6[CH2:105][CH2:104][C@@:103]6([CH3:111])[C@H:91]7[CH2:92][CH2:93][C@@H:94]6[C@H:95]([CH3:102])[CH2:96][CH2:97][CH2:98][CH:99]([CH3:101])[CH3:100])[CH2:86]5)[N:80]=[N:79]4)[C@H:72]3[OH:134])[C@H:46]2[OH:143])[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

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 866582803-{4-(Cholestan-3beta-yl-oxymethyl)-[1,2,3]triazol-1-yl}propyl 2,3,4,6-tetra-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranoside

Product 1

HCID 86658283HCID 86658283, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The perbenzoate 58 (70 mg, 0.0341 mmol) was dissolved in anhydrous THF (2 mL) and MeOH (2 mL). The mixture was treated with a solution of 11M NaOMe in MeOH (0.2 mL, 2.2 mmol). After stirring at r.t for 2 days, the white suspension was neutralized by addition of AG50WX8 resin (H+ form). The clear solution was separated from the resin by filtration. The resin was washed with MeOH (3×2 mL). The combined filtrate and washings were evaporated to dryness and dried in vacuum dessicator under P2O5 o/n to give the polyol 59, used directly in the next step.

Workup

  1. additionthe white suspension was neutralized by addition of AG50WX8 resin (H+ form)
  2. customThe clear solution was separated from the resin by filtration
  3. washThe resin was washed with MeOH (3×2 mL)
  4. customThe combined filtrate and washings were evaporated to dryness
  5. customdried in vacuum dessicator under P2O5 o/n

Sources & evidence

ORD record
ord-ab67d2393c92437387dc13f608bb0089
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Linked notes

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