D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate) Chemical Properties

Boiling point:

558.0±50.0 °C(Predicted)

Density 

1.28±0.1 g/cm3(Predicted)

D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate) Usage And Synthesis

Synthesis

D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate) is synthesised by reacting D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone with 4-Methylbenzoyl chloride in a pyridine solution. Yield: 95%. The specific reaction process and steps are as follows^[1]:
(1) Add toluoyl chloride (15.2 g) to a solution of (4S,5R)-5-ethynyl-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one (7.5 g) in pyridine (38 mL) at 0 °C.
(2) Stir the resulting mixture for 2 hours at 0 °C.
(3) Add water (45 mL) slowly at 0-5 °C, causing the product to crystallize.
(4) Filter the reaction mixture.
(5) Wash the filter cake with ice water.
(6) Dry the product.

References

[1] MARK MCLAUGHLIN*. Enantioselective Synthesis of 4′-Ethynyl-2-fluoro-2′-deoxyadenosine (EFdA) via Enzymatic Desymmetrization[J]. Organic Letters, 2017, 19 4: 926-929. DOI:10.1021/acs.orglett.7b00091.