Imidazole → HCID 14991429, compound

HRID 1196966Notes

Reaction equation

HRID 1196966 reaction equation
N1C=CN=C1.[S:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C@@H:7]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9].[Si:24](Cl)([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CO>CN(C=O)C.C(Cl)Cl.CCCCCC.CCOC(C)=O>[Si:24]([O:17][CH2:16][C@H:14]1[O:15][C@@H:7]([S:6][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C@H:8]([OH:9])[C@@H:10]([OH:11])[C@@H:12]1[OH:13])([C:37]([CH3:40])([CH3:39])[CH3:38])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 4

HCID 795ImidazoleHCID 887Methanol2×HCID 94078tert-ButyldiphenylchlorosilaneHCID 10934592Phenyl 1-thio-beta-D-glucopyranoside

Product 1

HCID 14991429HCID 14991429, compoundYield 90.6%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Imidazole (32 g) is added to a solution of 3 (30 g) in DMF (225 mL). After cooling to 0° C., tert-butyldiphenylsilyl chloride (34 g) is added. The reaction is allowed to come to room temperature overnight, whereupon TLC analysis (silica, 10% MeOH in CH2Cl2) indicates that the reaction is complete. MeOH (30 mL) is added and the reaction is stirred for an additional 30 minutes. The solvents are then removed in vacuo (40° C., 10 mm Hg). The residue is dissolved in EtOAc (500 mL) and washed successively with water (2×100 mL) and brine (2×100 mL). The EtOAc solution is then dried (MgSO4) and filtered. Removal of the EtOAc in vacuo provides a syrup which is subjected to flash column chromatography (silica, 5% EtOAc in hexane) to provide phenyl 6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside (4, 51 g).

Workup

  1. customThe solvents are then removed in vacuo (40° C., 10 mm Hg)
  2. dissolutionThe residue is dissolved in EtOAc (500 mL)
  3. washwashed successively with water (2×100 mL) and brine (2×100 mL)
  4. dry with materialThe EtOAc solution is then dried (MgSO4)
  5. filtrationfiltered
  6. customRemoval of the EtOAc in vacuo
  7. customprovides a syrup which

Sources & evidence

ORD record
ord-5c24a39e12884ffb9eb27823fea68637
Source dataset
uspto-grants-1992_05
Patent number
US05116821

Reaction notes

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