2-deoxy-2,2-difluoro-α-D-arabinofuranose (P_R)-1-O-phenyl-(neopentoxy-alaninyl)phosphate

Base Information

• Chemical Name: 2-deoxy-2,2-difluoro-α-D-arabinofuranose (P_R)-1-O-phenyl-(neopentoxy-alaninyl)phosphate
• CAS No.: 1430067-58-5
• Molecular Formula: C₁₉H₂₈F₂NO₈P
• Molecular Weight: 467.404

Synonyms:2-deoxy-2,2-difluoro-α-D-arabinofuranose (P_R)-1-O-phenyl-(neopentoxy-alaninyl)phosphate

Chemical Property of 2-deoxy-2,2-difluoro-α-D-arabinofuranose (P_R)-1-O-phenyl-(neopentoxy-alaninyl)phosphate

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Technology Process of 2-deoxy-2,2-difluoro-α-D-arabinofuranose (P_R)-1-O-phenyl-(neopentoxy-alaninyl)phosphate

There total 2 articles about 2-deoxy-2,2-difluoro-α-D-arabinofuranose (P_R)-1-O-phenyl-(neopentoxy-alaninyl)phosphate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C35H40F2NO12P (1443987-51-6) → 2-deoxy-2,2-difluoro-β-D-arabinofuranose (PR)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-56-3) + 2-deoxy-2,2-difluoro-β-D-arabinofuranose (PS)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-57-4) + 2-deoxy-2,2-difluoro-α-D-arabinofuranose (PR)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-58-5) + 2-deoxy-2,2-difluoro-α-D-arabinofuranose (PS)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-59-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; at 20 ℃; for 2h;

DOI:10.1016/j.bmcl.2013.02.117

Reference yield:

(2S)-2,2-dimethylpropyl 2-(chloro(phenoxy)phosphorylamino)propanoate (220592-65-4) + 2-deoxy-2,2-difluoro-3,5-di-O-benzyloxycarbonyl-D-arabinofuranose → 2-deoxy-2,2-difluoro-β-D-arabinofuranose (PR)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-56-3) + 2-deoxy-2,2-difluoro-β-D-arabinofuranose (PS)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-57-4) + 2-deoxy-2,2-difluoro-α-D-arabinofuranose (PR)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-58-5) + 2-deoxy-2,2-difluoro-α-D-arabinofuranose (PS)-1-O-phenyl-(neopentoxy-alaninyl)phosphate (1430067-59-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tert-butylmagnesium chloride / tetrahydrofuran / 0.33 h / 0 °C

1.2: 0 - 20 °C

2.1: hydrogen; palladium 10% on activated carbon / ethanol / 2 h / 20 °C

With palladium 10% on activated carbon; tert-butylmagnesium chloride; hydrogen; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmcl.2013.02.117

upstream raw materials:

(2S)-2,2-dimethylpropyl 2-(chloro(phenoxy)phosphorylamino)propanoate

C₃₅H₄₀F₂NO₁₂P

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