Water → 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

HRID 1464362Notes

Reaction equation

HRID 1464362 reaction equation
[CH3:1][CH:2]([CH3:36])[CH2:3][C@@H:4]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[C:5]([CH2:23][CH:24]=C)([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].I([O-])(=O)(=O)=O.[Na+].C(OCC)C.[OH2:48]>[Os](=O)(=O)(=O)=O>[CH:24]([CH2:23][C:5]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])([C:6]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:7])[C@H:4]([C:26]([O:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)=[O:27])[CH2:3][CH:2]([CH3:36])[CH3:1])=[O:48]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 23667635Sodium periodate2×HCID 678262121,2-dibenzyl 1-tert.butyl 4-methyl-1-(prop-2-en-1yl)-1,1,2(R)-pentanetricarboxylate

Product 1

HCID 867477791,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

A mixture of 1.23 g of 1,2-dibenzyl 1-tert.butyl 4-methyl-1-(prop-2-en-1yl)-1,1,2(R)-pentanetricarboxylate, 3 ml of a 1% aqueous solution of osmium tetroxide, 2.44 g of sodium periodate, 15 ml of diethyl ether and 15 ml of water was stirred at room temperature for 1 hour. A further 3.25 g of sodium periodate were added and the mixture was stirred at room temperature for 24 hours. The ether layer was separated and the aqueous layer was extracted with diethyl ether. The combined ether layers were washed repeatedly with 5% aqueous ascorbic acid solution and saturated sodium chloride solution. After drying over magnesium sulfate, the solution was evaporated and the residue was purified by flash chromatography on silica gel using hexane/diethyl ether (8:1) for the elution. There was obtained 0.955 g of 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil; MS: 497 (M+H)+.

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. customThe ether layer was separated
  3. extractionthe aqueous layer was extracted with diethyl ether
  4. washThe combined ether layers were washed repeatedly with 5% aqueous ascorbic acid solution and saturated sodium chloride solution
  5. dry with materialAfter drying over magnesium sulfate
  6. customthe solution was evaporated
  7. customthe residue was purified by flash chromatography on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-d6f70bcbcb2d4c6aa5bd7cb36d6fed18
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

Loading…