1-Desoxy-1-iodo-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranose → (3R,6R,7R,8R)-8-Isopropenyl-6,7-dimethoxy-1,4-dioxaspiro[2,5]octan-8-ol

HRID 234608Notes

Reaction equation

HRID 234608 reaction equation
I[CH2:2][C@:3]1([O:14][CH2:13][C@@H:10]([O:11][CH3:12])[C@@H:7]([O:8][CH3:9])[C@@:5]1([C:15]([CH3:17])=[CH2:16])[OH:6])[OH:4]>O1CCOCC1.[Ag-]=O>[C:15]([C@:5]1([OH:6])[C@:3]2([O:4][CH2:2]2)[O:14][CH2:13][C@@H:10]([O:11][CH3:12])[C@H:7]1[O:8][CH3:9])([CH3:17])=[CH2:16]

Participants

4

Reactant 1

HCID 867502171-Desoxy-1-iodo-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranose

Product 1

HCID 22869080(3R,6R,7R,8R)-8-Isopropenyl-6,7-dimethoxy-1,4-dioxaspiro[2,5]octan-8-olYield 95.9%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2.20 g (9.49 mmol) of silver(I) oxide are added in portions, over a period of 48 hours, to a solution of the compound obtained in Example 31 (0.52 g; 1.45 mmol) in 5 ml of dioxane. The reaction mixture is then filtered and the filtrate is evaporated to give 0.32 g (1.39 mmol) of the desired product in the form of a white solid.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-f8522ab08d8d4863b417b3c74ee232eb
Source dataset
uspto-grants-1997_01
Patent number
US05595976

Reaction notes

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