D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate)
- Product Name
- D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate)
- CAS No.
- 2072080-27-2
- Chemical Name
- D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate)
- Synonyms
- D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate)
- CBNumber
- CB29926745
- Molecular Formula
- C23H20O6
- Formula Weight
- 392.4
- MOL File
- 2072080-27-2.mol
D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate) Property
- 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) Chemical Properties,Usage,Production
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.
D-erythro-Pentonic acid, 2-deoxy-4-C-ethynyl-, γ-lactone, 3,5-bis(4-methylbenzoate) Preparation Products And Raw materials
Raw materials
Preparation Products
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