Sodium prop-2-enolate → (2S,3S,4S,5R,6S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(2-[1,3]dioxolan-2-yl-4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid

HRID 1820605Notes

Reaction equation

HRID 1820605 reaction equation
C([O-])C=C.[Na+].C([O:9][C:10]([C@H:12]1[C@H:17]([O:18][Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20])[C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C@@H:15]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[C@H:14]([O:42][C:43]2[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:44]=2[CH:52]2[O:56][CH2:55][CH2:54][O:53]2)[O:13]1)=[O:11])C=C>C(O)C=C>[C:22]([Si:19]([CH3:21])([CH3:20])[O:18][C@@H:17]1[C@H:16]([O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[C@@H:15]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])[CH3:37])[C@H:14]([O:42][C:43]2[CH:48]=[CH:47][C:46]([N+:49]([O-:51])=[O:50])=[CH:45][C:44]=2[CH:52]2[O:56][CH2:55][CH2:54][O:53]2)[O:13][C@@H:12]1[C:10]([OH:11])=[O:9])([CH3:23])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 23669913Sodium prop-2-enolateHCID 68983558(2R,3S,4S,5R,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(2-[1,3]dioxolan-2-yl-4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid allyl ester

Product 1

HCID 68982700(2S,3S,4S,5R,6S)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-6-(2-[1,3]dioxolan-2-yl-4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acidYield 100.4%

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent2×

Conditions

Temperature
50 °C

Procedure

The solution of 5.64 g (7.58 mmol) of the compound, presented according to Example LE3d, in 150 ml of allyl alcohol is mixed with 9.1 ml of a 1 M solution of sodium allyl alcoholate in allyl alcohol, and it is stirred for 2.5 hours at 50° C. It is concentrated by evaporation, mixed with water, extracted several times with dichloromethane, the combined organic extracts are washed with saturated sodium chloride solution and dried on magnesium sulfate. The residue that is obtained after filtration and removal of the solvent is purified by chromatography on fine silica gel, and 1.78 g (2.44 mmol, 32%) of the title compound as well as 1.87 g (2.43 mmol, 32%) of (2R,3S,4S,5R,6S)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-6-(2-[1,3]dioxolan-2-yl-4-nitro-phenoxy)-tetrahydro-pyran-2-carboxylic acid allyl ester are isolated.

Workup

  1. concentrationIt is concentrated by evaporation
  2. additionmixed with water
  3. extractionextracted several times with dichloromethane
  4. washthe combined organic extracts are washed with saturated sodium chloride solution
  5. customdried on magnesium sulfate
  6. customThe residue that is obtained
  7. filtrationafter filtration and removal of the solvent

Sources & evidence

ORD record
ord-23b623758f31488d8f71058893e410fc
Source dataset
uspto-grants-2009_10
Patent number
US07605136B2

Reaction notes

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