Sodium Azide → 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide

HRID 74846Notes

Reaction equation

HRID 74846 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@H:28]([O:36][C@@H:37]2[C@@H:42]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[O:41][C@H:40](Br)[C@H:39]([O:49][C:50](=[O:52])[CH3:51])[C@H:38]2[O:53][C:54](=[O:56])[CH3:55])[C@H:27]([O:57][C:58](=[O:60])[CH3:59])[C@H:26]1[O:61][C:62](=[O:64])[CH3:63])(=[O:3])[CH3:2].[N-:65]=[N+:66]=[N-:67].[Na+]>CCOC(C)=O.C([O-])(O)=O.[Na+].[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[O:7][C@@H:6]1[O:24][C@@H:25]1[C@@H:30]([CH2:31][O:32][C:33](=[O:35])[CH3:34])[O:29][C@H:28]([O:36][C@@H:37]2[C@@H:42]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[O:41][C@@H:40]([N:65]=[N+:66]=[N-:67])[C@H:39]([O:49][C:50](=[O:52])[CH3:51])[C@H:38]2[O:53][C:54](=[O:56])[CH3:55])[C@H:27]([O:57][C:58](=[O:60])[CH3:59])[C@H:26]1[O:61][C:62](=[O:64])[CH3:63])(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 13055893Glc2Ac3Ac4Ac6Ac(a1-4)Glc2Ac3Ac6Ac(a1-4)a-Glc1Br2Ac3Ac6Ac

Product 1

HCID 112053312,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-alpha-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

The bromide 72 (˜200 mg) was taken up in a mixture of EtOAc (5 mL) and NaHCO3 (sat.) (5 mL). NaN3 (500 mg) was added, followed by Bu4NBr (cat.). The mixture was stirred vigorously overnight at r.t. The solution was diluted with EtOAc and washed with NaHCO3(sat.) (×2) and brine (×1), before being dried (Na2SO4) and the solvent evaporated to yield the azide 73 as white solid (198.9 mg, 100%, two steps) which was reacted on without further purification or characterisation.

Workup

  1. washwashed with NaHCO3(sat.) (×2) and brine (×1)
  2. dry with materialbefore being dried (Na2SO4)
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-2ed70d329e29466ea370805af3279a42
Source dataset
uspto-grants-2014_09
Patent number
US08828952B2

Reaction notes

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