Imidazole → (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol

HRID 60718

Reaction equation

HRID 60718 reaction equation
[O:1]=[CH:2][C@H:3]([C@@H:5]([C@@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].N1C=CN=C1.[C:16]([Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:19])([CH3:18])[CH3:17]>CN(C=O)C.CCOC(C)=O>[Si:20]([O:1][CH2:2][C@H:3]1[O:4][C@@H:9]([OH:10])[C@@H:7]([OH:8])[CH:5]1[OH:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 66308D-ArabinoseHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 131737102(2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triolYield 25.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of D-arabinose (50 g, 0.33 mol) in DMF (500 mL) was added imidazole (45 g, 0.66 mol) and tert-butylchlorodiphenylsilane (109 g, 0.4 mol). After being stirred at room temperature for 2 hours, the resulting solution was diluted with EtOAc (2000 mL), washed with water, brine and dried over Na2SO4. The organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (eluting with 1:11 EtOAc in petroleum ether) to afford 33 g of (2R,3S,5R)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]tetrahydrofuran-2,3,4-triol (compound 25a).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. concentrationThe organic layer was concentrated in vacuo
  4. customthe residue was purified by column chromatography on silica gel (eluting with 1:11 EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-8f78f4534f214d0aa8ff1322a63c61e7
Source dataset
uspto-grants-2016_09
Patent number
US09441008B2

Linked notes

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