1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate synthesis

2synthesis methods

Product Name:1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate
CAS Number:143157-24-8
Molecular formula:C23H18F2N2O7
Molecular Weight:472.39

D-erythro-Pentofuranose, 2-deoxy-2,2-difluoro-, 1-acetate 3,5-dibenzoate

890044-84-5
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10457-14-4
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1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate

143157-24-8
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$149.90/10mg

143157-27-1 Synthesis

2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate

143157-27-1
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Yield:95 % de

Reaction Conditions:

with tin(IV) chloride in 1,2-dichloro-ethane at 20 - 83; for 22 h;Product distribution / selectivity;

Steps:

2

A 0.46 g sample of l-acetyl-2-deoxy-3,5-dibenzoate-2,2-difluoro-ribofuranose(compound IV that can be obtained from commercially available material e.g. by method EPO > C T . - 8 ,1 S if, fi S: / ^' H- H ^' 3 & '9 reported in patent application WO2005095430) was dissolved in 15 ml of dichloroethane, and 1.26 g of 2,4-bis-O-trimethylsilyluracil and 0.89 ml Of SnCl₄ were added at room temperature. The mixture was then heated to 83°C for 22 hours. The mixture was then allowed to cool to room temperature, and quenched via addition of 20 ml of a saturated sodium bicarbonate solution. The suspension was filtered over a pad of Celite eluting with 100 ml of dichloromethane. The filtrate was washed with 20 ml of saturated sodium bicarbonate solution, dried over Na₂SO₄, and filtered and concentrated under reduced pressure to obtain an off-white foam.[00047] The crude product, a 1 :5 mixture of anomers, was triturated in a 2: 1 heptane/ethyl acetate mixture, and filtered. The undissolved solid was identified (IH, 19F NMR, HPLC) as /3-anomer (95% de) of the title compound.¹H NMR: δ (300 MHz, DMSO): 11.65 (IH, s); 8.10 (2H, d); 7.90 (2H, d); 7.80-7.42 (7H, m);6.37 (IH, t); 5.95-5.85 (IH, m); 5.77 (1, d); 4.92-4.85 (3H, m)

References:

WO2006/63105,2006,A1 Location in patent:Page/Page column 11-12

2-Deoxy-2,2-difluoro-D-ribofuranose-3,5-dibenzoate-1-methanesulfonate

134877-42-2
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10457-14-4
71 suppliers
$65.00/10mg

143157-24-8
11 suppliers
$149.90/10mg

143157-27-1 Synthesis

143157-27-1
24 suppliers
$70.00/10mg

References