Thioglycerol → HCID 57196533, compound

HRID 1197041Notes

Reaction equation

HRID 1197041 reaction equation
O1[CH:6]2[CH:2]1[C:3](=[O:34])[CH:4]([CH:23]([OH:33])[C:24]#[C:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:5]2[CH:7]=[CH:8][CH:9]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:10]1[CH2:14][CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C.[OH:42][CH:43]([CH2:46][OH:47])[CH2:44][SH:45].S([O-])(O)(=O)=O.[K+]>CO>[OH:42][CH:43]([CH2:46][OH:47])[CH2:44][S:45][C:2]1[C:3](=[O:34])[CH:4]([CH:23]([OH:33])[C:24]#[C:25][CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:5]([CH:7]=[CH:8][CH:9]([O:15][Si:16]([C:19]([CH3:22])([CH3:20])[CH3:21])([CH3:18])[CH3:17])[CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:6]=1

Participants

6

Reactant 4

HCID 7291ThioglycerolHCID 8471TriethylamineHCID 516920Potassium bisulfateHCID 54486752HCID 54486752, compound

Product 1

HCID 57196533HCID 57196533, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 49 mg amount of 2,3-epoxy-5-(1-hydroxy-6-methoxycarbonyl-2-hexynyl)-4-(3-t-butyldimethylsilyloxy-3-cyclopentyl-1-propenyl)cyclopentanone was dissolved in 1 ml of methanol and 21 μl of triethylamine was added. Then, 12 mg of 2,3-dihydroxypropanethiol was added thereto, followed by stirring for 2 hours. The reaction mixture was poured on an aqueous saturated solution of potassium hydrogen sulfate, followed by extracting with ethyl acetate. The extracted solution was washed with a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. After filtering and concentrating, the concentrate was subjected to silica gel chromatography to give 36 mg (yield 62%) of 2-(2,3-dihydroxypropylthio)-5-(1-hydroxy-6-methoxycarbonyl-2-hexynyl)-4-(3-t-butyldimethylsilyloxy-3-cyclopentyl-1-propenyl)-2-cyclopentenone.

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe extracted solution was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtering
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-f42a16b307b44042baff0f5c45fd8ad1
Source dataset
uspto-grants-1992_05
Patent number
US05116869

Reaction notes

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