2-(Trimethylsilyl)ethanol → HCID 53909159, compound

HRID 1683155Notes

Reaction equation

HRID 1683155 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[N:21]=[N+:22]=[N-:23])(=[O:3])[CH3:2].[CH3:24][Si:25]([CH3:30])([CH3:29])[CH2:26][CH2:27][OH:28]>C(Cl)Cl.[Si]([O-])([O-])([O-])[O-].[Ag+].[Ag+].[Ag+].[Ag+]>[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]([O:28][CH2:27][CH2:26][Si:25]([CH3:30])([CH3:29])[CH3:24])[C@@H:6]1[N:21]=[N+:22]=[N-:23])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 180132-(Trimethylsilyl)ethanolHCID 10872911HCID 10872911, compound

Product 1

HCID 53909159HCID 53909159, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 86733097HCID 86733097, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl bromide (6 g, 15.2 mmol), 2-(trimethylsilyl)-ethanol (2.7 g, 22.8 mmol) and powdered molecular sieves 4 Å (14.6 g) in dry CH2Cl2 (100 ml) was stirred under N2 for 1 h. Silver silicate (369) was added. After 20 min. stirring, the reaction mixture was filtered through celite and the filtrate was evaporated to dryness. Column chromatography (heptane-EtOAc 3:1) of the residue gave 23 (5.11 g, 78%) as a syrup. [α]D25 -18° (c 1, CHCl3).

Workup

  1. filtrationthe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2da8c6df55aa41a79ce07c7b36e96c86
Source dataset
uspto-grants-1997_06
Patent number
US05637569

Reaction notes

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