Methanol → HCID 58786156, compound

HRID 1375975Notes

Reaction equation

HRID 1375975 reaction equation
[BH4-].[Na+].[CH3:3][O:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:11]=[C:12]([C@H:14]2[C@H:19]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C@@H:18]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:17]([O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[O:15]2)[CH:13]=1)[CH:9]=[O:10].CO.C1COCC1>O.CC(C)=O>[CH2:21]([O:20][C@@H:19]1[C@@H:18]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@H:17]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:16]([CH2:44][O:45][CH2:46][C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[O:15][C@H:14]1[C:12]1[CH:13]=[C:6]([CH2:5][O:4][CH3:3])[CH:7]=[C:8]([CH2:9][OH:10])[CH:11]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 58786127HCID 58786127, compound

Product 1

HCID 58786156HCID 58786156, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Sodium borohydride (0.15 g) was added to a solution of 3-methoxymethyl-5-[(2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzaldehyde (2.6 g) in a 1:1 mixture of methanol and THF (10 ml) and the mixture was stirred for one hour. Acetone (5.0 ml) was added to the reaction mixture and the mixture was stirred for 10 minutes. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[3-(hydroxymethyl)-5-(methoxymethyl) phenyl]-D-glucitol (2.1 g).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-789599c8596a437895e5be462671a8f1
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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