Diiodomethane → HCID 71110835, compound

HRID 576426Notes

Reaction equation

HRID 576426 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([OH:27])[CH:21]=1.[C:28]([O-])([O-])=O.[K+].[K+].C(I)I>CN(C=O)C>[O:26]1[C:23]2[CH:24]=[CH:25][C:20]([CH2:19][C:3]3[CH:4]=[C:5]([C@H:8]4[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17][OH:18])[O:9]4)[CH:6]=[CH:7][C:2]=3[Cl:1])=[CH:21][C:22]=2[O:27][CH2:28]1

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 11430Potassium CarbonateHCID 71110830(2S,3R,4R,5S,6R)-2-(4-chloro-3-(3,4-dihydroxybenzyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

Product 1

HCID 71110835HCID 71110835, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (2S,3R,4R,5S,6R)-2-(4-chloro-3-(3,4-dihydroxybenzyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol (E055) (30 mg, 0.0756 mmole) in DMF (4 mL) were added K2CO3 and CH2I2 (7.3 μL). The reaction mixture was stirred at 100° C. overnight and filtered. The resulting crude solution was purified by reverse phase preparative HPLC to yield the title compound (16 mg, 0.0401 mmole, 53%) as a brown gum.

Workup

  1. filtrationfiltered
  2. customThe resulting crude solution was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-72326ab78d7d45b38c2e241c54e42ec9
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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