Intermediate of API

817204-32-3

  • Product Name：(2'R)-N-Benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine -3',5'-dibenzoate
  • Molecular Formula：C31H26FN3O7
  • Specifications：99%
  • Molecular Weight：571.562
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Product Details;

CasNo： 817204-32-3

Molecular Formula： C31H26FN3O7

Fast Delivery High Quality (2'R)-N-Benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine -3',5'-dibenzoate 817204-32-3 For Sale

  • Molecular Formula:C31H26FN3O7
  • Molecular Weight:571.562
  • Melting Point:241 oC (dichloromethane/hexane) 
  • PKA:8.51±0.20(Predicted) 
  • PSA：125.82000 
  • Density:1.34±0.1 g/cm3 (20 oC,760 mmHg) 
  • LogP:4.27680 

(2'R)-N-Benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine -3',5'-dibenzoate(Cas 817204-32-3) Usage

Uses

(2'R)-N-Benzoyl-2'-deoxy-2'-fluoro-2'-methylcytidine -3',5'-dibenzoate is an impurity of Sofosbuvir (P839640). To support clinical development efforts, we needed an efficient and scalable synthesis of PSI-6130.

IUPAC Name: [(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-3-benzoyloxy-4-fluoro-4-methyloxolan-2-yl]methyl benzoate  
Isomeric SMILES: C[C@]1([C@@H]([C@H](O[C@H]1N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)COC(=O)C4=CC=CC=C4)OC(=O)C5=CC=CC=C5)F  
InChIKey: MXEQSUUFNWPUJH-RDWHIKKYSA-N  
InChI: InChI=1S/C31H26FN3O7/c1-31(32)25(42-28(38)22-15-9-4-10-16-22)23(19-40-27(37)21-13-7-3-8-14-21)41-29(31)35-18-17-24(34-30(35)39)33-26(36)20-11-5-2-6-12-20/h2-18,23,25,29H,19H2,1H3,(H,33,34,36,39)/t23-,25-,29-,31-/m1/s1  

817204-32-3 Relevant articles

A General and Enantioselective Approach to Pentoses: A Rapid Synthesis of PSI-6130 (817204-32-3), the Nucleoside Core of Sofosbuvir

Manuel Peifer, Raphaëlle Berger, Valerie W. Shurtleff, Jay C. Conrad, and David W. C. MacMillan*

J. Am. Chem. Soc. 2014, 136, 16, 5900–5903

Sofosbuvir (vide supra) has recently been approved as a therapeutic agent for the treatment of hepatitis C. This prodrug is synthesized via the late-stage nucleoside intermediate PSI-6130 (817204-32-3), which we hypothesized could be accessed rapidly using our pentose strategy.

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Through systematical comparison of vario...

817204-32-3 Process route

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate
1500076-79-8

(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
85743-99-3

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
817204-32-3

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Conditions
Conditions Yield
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; In chlorobenzene; at 23 ℃; for 0.25h;
With tin(IV) chloride; In chlorobenzene; at 50 - 60 ℃; for 18h;
72.5%
With tin(IV) chloride; In chlorobenzene; at 75 ℃;
65%
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; With tin(IV) chloride; In chlorobenzene; at 70 ℃; for 10h;
With water; sodium hydrogencarbonate; In dichloromethane; chlorobenzene; at 10 - 45 ℃; for 0.5h;
 
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; With tin(IV) chloride; In dichloromethane; at 30 - 80 ℃; for 20h; under 1875.19 Torr; Sealed tube;
With acetic acid; In dichloromethane; water; at 18 - 25 ℃;
34.9 g
(2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate; N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide; With tin(IV) chloride; In dichloromethane; at 75 - 80 ℃; for 20h; under 1875.19 Torr;
With acetic acid; In dichloromethane; water; at 18 - 25 ℃;
34.9 g
((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methylbenzoate

((2R,3R,4R,5R)-3-(benzoyloxy)-5-chloro-4-fluoro-4-methyltetrahydrofuran-2-yl)methylbenzoate

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide
85743-99-3

N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate
817204-32-3

(2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate

Conditions
Conditions Yield
With tin(IV) chloride; acetic acid; In dichloromethane; chlorobenzene; at 70 - 85 ℃; for 0.0166667h; under 750.075 - 2250.23 Torr; Reagent/catalyst; Temperature; Pressure;
72%

817204-32-3 Upstream products

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    1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-2-C-methyl-D-ribofuranose

  • 1500076-79-8
    1500076-79-8

    (2R)-2-deoxy-2-fluoro-2-methyl-α/β-D-erythro-pentofuranosyl chloride-3,5-dibenzoate

  • 85743-99-3
    85743-99-3

    N-(2-Trimethylsilanyloxy-pyrimidin-4-yl)-benzamide

817204-32-3 Downstream products

  • 817204-33-4
    817204-33-4

    (2'R)-2'-deoxy-2'-fluoro-2'-methylcytidine

  • 863329-65-1
    863329-65-1

    (2‘R)-2‘-deoxy-2’-fluoro-2-methyluridine-3’,5’-dibenzoate

  • 863329-66-2
    863329-66-2

    2'-deoxy-2'-fluoro-2'-methyluridine

  • 1064684-44-1
    1064684-44-1

    sofosbuvir

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