HCID 6420437, compound → HCID 10868519, compound

HRID 2060945Notes

Reaction equation

HRID 2060945 reaction equation
CC(S[CH:5]1[CH:9]2[O:10][C:11]([CH3:14])([CH3:13])[O:12][CH:8]2[O:7][CH:6]1[CH:15]1[O:19][C:18]([CH3:21])([CH3:20])[O:17][CH2:16]1)=O>CO.[Ni].[Al].[Ni]>[CH3:20][C:18]1([CH3:21])[O:19][C@@H:15]([C@H:6]2[O:7][C@@H:8]3[O:12][C:11]([CH3:14])([CH3:13])[O:10][C@@H:9]3[CH2:5]2)[CH2:16][O:17]1

Participants

5

Reactant 1

HCID 6420437HCID 6420437, compound

Product 1

HCID 10868519HCID 10868519, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 6336846Nickel aluminideCatalystHCID 887MethanolSolvent2×

Procedure

The crude reaction mixture obtained by the procedure described in Example 2 containing 3-S-Acetyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-allofuranose E2 (7.5 g, 23.58 mmole) was dissolved in methanol and added to a slurry of freshly prepared Raney nickel (prepared from nickel-aluminium alloy, 60 g) in methanol (100 ml). The reaction mixture was stirred at room temperature for 15 h and filtered. The filtrate was concentrated under reduced pressure to give the title product E3; yield: 5 g, 88%, which was subjected to the following step without further purification.

Workup

  1. customThe crude reaction mixture
  2. customobtained by the procedure
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-feb223d912e848f0a163d80de59a498f
Source dataset
uspto-grants-2012_10
Patent number
US08278468B2

Reaction notes

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