HCID 87366190, compound → HCID 87367150, compound

HRID 1670048Notes

Reaction equation

HRID 1670048 reaction equation
C([O:9][CH:10]([CH2:52][O:53][C@H:54]1[O:83][C@H:82]([CH2:84][O:85][CH2:86][C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=2)[C@@H:73]([O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C@H:64]([O:65][CH2:66][C:67]2[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=2)[C@@H:55]1[O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[CH2:11][O:12][C@H:13]1[O:42][C@H:41]([CH2:43][O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@@H:32]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@@H:14]1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=O)C1C=CC=CC=1>C[O-].[Na+].CO>[CH2:16]([O:15][C@H:14]1[C@@H:23]([O:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C@H:32]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C@@H:41]([CH2:43][O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:42][C@@H:13]1[O:12][CH2:11][CH:10]([CH2:52][O:53][C@H:54]1[O:83][C@H:82]([CH2:84][O:85][CH2:86][C:87]2[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=2)[C@@H:73]([O:74][CH2:75][C:76]2[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=2)[C@H:64]([O:65][CH2:66][C:67]2[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=2)[C@@H:55]1[O:56][CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[OH:9])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 1

HCID 87366190HCID 87366190, compound

Product 1

HCID 87367150HCID 87367150, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 10942334Sodium MethoxideSolvent

Procedure

Dimannoside 11 (800 mg, 0.65 mmol) was dissolved in 1M sodium methoxide in methanol (80 mL) and the reaction was stirred overnight at room temperature. The solvent was removed and the residue was dissolved in dichloromethane, washed with 2M HCl (2×50 mL) and water (50 mL), and dried over magnesium sulfate. Removal of the solvent gave a residue (a to β 4:1, 615 mg) which was purified over silica [hexane/ether 75:25 to 65:35 gradient elution] to afford the title compound 12 (470 mg, 64%), a mixture of 12 and 13 (90 mg, 12%), and 13 (40 mg, 5%).

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with 2M HCl (2×50 mL) and water (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent
  6. customgave a residue (a to β 4:1, 615 mg) which
  7. customwas purified over silica [hexane/ether 75:25 to 65:35 gradient elution]

Sources & evidence

ORD record
ord-9aee9225a52b42ad863eaa150f403f33
Source dataset
uspto-grants-2011_08
Patent number
US07989602B2

Reaction notes

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