1,4-Dibromo-2,3-butanediol → Threitol bis-phosphorothioate tetrahydrate

HRID 1598393Notes

Reaction equation

HRID 1598393 reaction equation
Br[CH2:2][CH:3]([OH:8])[CH:4]([OH:7])[CH2:5]Br.[OH2:9].[OH2:10].O.O.O.O.O.O.O.O.O.O.[P:21]([O-:25])([O-:24])([O-:23])=[S:22].[Na+].[Na+].[Na+]>CN(C=O)C.O.[N+]([O-])([O-])=O.[Ag+]>[OH2:7].[OH2:23].[OH2:9].[OH2:7].[P:21](=[S:22])([OH:25])([OH:24])[OH:23].[P:21](=[S:22])([OH:25])([OH:24])[OH:23].[CH2:2]([OH:10])[C@H:3]([C@@H:4]([CH2:5][OH:9])[OH:7])[OH:8]

Participants

6

Reactant 2

HCID 985121,4-Dibromo-2,3-butanediolHCID 45052183Sodium thiophosphate dodecahydrate

Product 1

HCID 86752373Threitol bis-phosphorothioate tetrahydrateYield 285%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,4-dibromo-2,3-butanediol (1.0 g, 4.0 mmol) in 5 ml DMF is added to sodium thiophosphate dodecahydrate (3.8 gm, 10.1 mmol) in 20 ml H2O. The mixture is stirred overnight at room temperature. A 5% silver nitrate solution is added to precipitate excess sodium thiophosphate. The precipitate is filtered out and the filtrate dried under high vacuum. The solid residue is triturated with methanol and filtered to yield 1.8 g (3.8 mmol) of threitol bis-phosphorothioate tetrahydrate.

Workup

  1. customto precipitate excess sodium thiophosphate
  2. filtrationThe precipitate is filtered out
  3. customthe filtrate dried under high vacuum
  4. customThe solid residue is triturated with methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-d8912c5171b5473da905689e586426fe
Source dataset
uspto-grants-1998_04
Patent number
US05736624

Reaction notes

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