2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol → 1-Amino-2,5-anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol

HRID 54814Notes

Reaction equation

HRID 54814 reaction equation
[N:1]([CH2:4][C@H:5]1[O:28][C@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:7]([OH:29])[CH2:6]1)=[N+]=[N-].[H][H]>[Pd].O1CCCC1>[NH2:1][CH2:4][C@H:5]1[O:28][C@H:8]([CH2:9][O:10][Si:11]([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:7]([OH:29])[CH2:6]1

Participants

5

Reactant 2

HCID 867503512,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitolHCID 178418361HCID 178418361, compound

Product 1

HCID 677073761-Amino-2,5-anhydro-1,3-dideoxy-6-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitolYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 3.78 g of product from Example 276, 0.562 g of 10% palladium on carbon and 50 ml of tetrahydrofuran is hydrogenated under a balloon of hydrogen for 1 hour. The reaction mixture is filtered and the filtrate is concentrated in vacuo to give 3.4 g of the desired product.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-93826211811b458ea6bc9d26f8ec3719
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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