HCID 53909159, compound → 2-(Trimethylsilyl)ethyl 2-azido-2-deoxy-beta-D-galactopyranoside

HRID 1683156Notes

Reaction equation

HRID 1683156 reaction equation
C([O:4][C@H:5]1[C@@H:17]([O:18]C(=O)C)[C@@H:16]([CH2:22][O:23]C(=O)C)[O:15][C@@H:7]([O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C@@H:6]1[N:27]=[N+:28]=[N-:29])(=O)C>C[O-].[Na+]>[N:27]([C@@H:6]1[C@@H:5]([OH:4])[C@@H:17]([OH:18])[C@@H:16]([CH2:22][OH:23])[O:15][C@H:7]1[O:8][CH2:9][CH2:10][Si:11]([CH3:13])([CH3:14])[CH3:12])=[N+:28]=[N-:29]

Participants

3

Reactant 1

HCID 53909159HCID 53909159, compound

Product 1

HCID 108597232-(Trimethylsilyl)ethyl 2-azido-2-deoxy-beta-D-galactopyranosideYield 94%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Compound 23 (4.88 g, 11.3 mmol) was stirred in methanolic NaOMe (0.04M, 50 ml) for 90 min. The mixture was decationised with Amberlite IR-120(H+) resin, filtered and evaporated to dryness to give 24 (3.24 g, 94%), [α]D25 +8.5° (c 0.8, MeOH), m.p. 158°-161° C. (ether-heptane).

Workup

  1. filtrationfiltered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-7eff57a15f2e46a6a938e4b7527edaee
Source dataset
uspto-grants-1997_06
Patent number
US05637569

Reaction notes

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