1,3-Propanedithiol → (2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
Reaction equation
O.[O:2]=[CH:3][C@@H:4]([C@@H:6]([C@H:8]([C@H:10]([CH3:12])[OH:11])[OH:9])[OH:7])[OH:5].C(S)CCS.[OH-].[Na+]>Cl>[O:2]=[CH:3][C@@H:4]([C@@H:6]([C@H:8]([C@H:10]([CH3:12])[OH:11])[OH:9])[OH:7])[OH:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
L-Rhamnose monohydrate (168.3 g, 0.92 mol) is added as a solid in portions, under strong stirring, to a mixture of 1,3-propanedithiol (100 g, 0.92 mol) in 500 ml of 37% HCl. The resulting solution is kept under stirring for 12 hours at about 20° C. Already at the first hour, formation of an abundant white precipitate is observed. The suspension is then cooled to 5-10° C. and the acid excess is neutralized with NaOH and 500 ml of ice. The suspension at pH of about 7 is then filtered and the solid is washed with water and 100 ml of isopropanol. The wet solid is dried under vacuum at 40° C. for 16 hours to attain 222 g of product (XII) as an off-white solid in 95% yield.
Workup
- temperatureThe suspension is then cooled to 5-10° C.
- filtrationThe suspension at pH of about 7 is then filtered
- washthe solid is washed with water and 100 ml of isopropanol
- customThe wet solid is dried under vacuum at 40° C. for 16 hours
Sources & evidence
- ORD record
- ord-4d7db13feb49488b94903e78f6567f10
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809553B2
Reaction notes
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