Azidotrimethylsilane → HCID 178476366, compound

HRID 417801Notes

Reaction equation

HRID 417801 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[O:8][C@H:7](Br)[C@@H:6]1[NH:21][C:22](=[C:24]1[C:29](=[O:30])[CH2:28][C:27]([CH3:32])([CH3:31])[CH2:26][C:25]1=[O:33])[CH3:23])(=[O:3])[CH3:2].C[Si]([N:38]=[N+:39]=[N-:40])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C>[N:38]([C@H:7]1[O:8][C@H:9]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:5]([O:4][C:1](=[O:3])[CH3:2])[C@H:6]1[NH:21][C:22](=[C:24]1[C:29](=[O:30])[CH2:28][C:27]([CH3:32])([CH3:31])[CH2:26][C:25]1=[O:33])[CH3:23])=[N+:39]=[N-:40]

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 178476345HCID 178476345, compound

Product 1

HCID 178476366HCID 178476366, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,4,6-tri-O-Acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide (3) (60 g, 0.112 mol) is suspended in acetonitrile (280 mL) and trimethylsilylazide (TMS-N3) (29.9 mL, 0.224 mol) is added dropwise followed by the dropwise addition of tetrabutylammonium fluoride (1 M TBAF in tetrahydrofuran) (225 mL, 0.225 mol). The reaction is stirred for 16 hr protected from light. The solvents are removed under reduced pressure, and the residue is preabsorbed on silica (150 g) and the product eluted with ethyl acetate/petroleum ether (1:1) (2 L). The solvents are evaporated and the crude residue used directly in the next step.

Workup

  1. customThe solvents are removed under reduced pressure
  2. customthe residue is preabsorbed on silica (150 g)
  3. washthe product eluted with ethyl acetate/petroleum ether (1:1) (2 L)
  4. customThe solvents are evaporated

Sources & evidence

ORD record
ord-c2b80c24b46148bebff70ff88aa3c283
Source dataset
uspto-grants-2012_01
Patent number
US08093227B2

Reaction notes

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