1-Butanaminium, N,N,N-tributyl-, azide → HCID 102391931, compound

HRID 876093Notes

Reaction equation

HRID 876093 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:14][C@@H:11]([O:12][CH3:13])[C@@H:10]1OS(C(F)(F)F)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:42]=[N+:43]=[N-:44].C([N+](CCCC)(CCCC)CCCC)CCC>C1C=CC=CC=1>[N:42]([C@H:10]1[C@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:14][C@H:11]1[O:12][CH3:13])=[N+:43]=[N-:44]

Participants

4

Reactant 2

HCID 57432321-Butanaminium, N,N,N-tributyl-, azideHCID 87307886HCID 87307886, compound

Product 1

HCID 102391931HCID 102391931, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Methyl 3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-α-L-mannopyranoside (6) (12.23 g) was dissolved in dehydrated benzene (400 ml), tetrabutylammonium azide [(n-Bu)4NN3] (29.16 g) was added thereto under an argon atmosphere. After 3 days, (n-Bu)4NN3 (3.61 g) was further added thereto. The mixture was stirred at room temperature for an additional 11 days (14 days in total). The reaction mixture was charged to a silica gel column as such to effect purification by silica gel column chromatography combined with preparative thin-layer chromatography, whereby a target product was obtained (yield: 3.58 g, yield ratio: 36%).

Workup

  1. additionThe reaction mixture was charged to a silica gel column as such
  2. custompurification by silica gel column chromatography
  3. customwas obtained
  4. custom(yield: 3.58 g, yield ratio: 36%)

Sources & evidence

ORD record
ord-af0f52d382f941919ecc1fc5993f1a72
Source dataset
uspto-grants-2015_03
Patent number
US08986656B2

Reaction notes

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