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

Base Information

• Chemical Name: 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate
• CAS No.: 143157-27-1
• Molecular Formula: C23H18F2N2O7
• Molecular Weight: 472.402
• Mol file: 143157-27-1.mol

Synonyms:2'-deoxy-2',2'-difluoro-3,5-dibenzoate-uridine;2'-deoxy-2',2'-difluorouridine-3',5'-dibenzoate;3,5-Dibenzoate-2,2-difluorouridine;21-deoxy-21,21-difluoro-3,5-di-O-benzoyl-uridine;2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate;

Chemical Property of 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate

Chemical Property:

• PKA: 9.39±0.10(Predicted)
• PSA: 116.95000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: 2.56420
• Solubility.: Dichloromethane, Methanol

Purity/Quality:

97% ^*data from raw suppliers

2’,2’-Difluoro-2’-deoxyuridine3'',5''-Dibenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Protected 2’,2’-Difluoro-2’-deoxyuridine, a Gemcitabine metabolite.

Technology Process of 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate

There total 9 articles about 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate 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: 90.0%

(2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate (1445381-44-1) → ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate (143157-27-1)

Guidance literature:

With acetic acid; Reflux;

DOI:10.1021/acsmedchemlett.0c00485

Reference yield: 72.0%

benzoyl chloride (98-88-4) + Deoxydifluorouridine (114248-23-6) → ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate (143157-27-1)

Guidance literature:

With 4-methyl-morpholine; dmap; In tetrahydrofuran; at 0 - 5 ℃; for 8h;

Reference yield:

21-deoxy-21,21-difluoro-3,5-bis-O-benzoyl-D-ribose trichloroacetimidate (908337-63-3) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → ((2R,3R,5R)-3-(benzoyloxy)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4,4-difluorotetrahydrofuran-2-yl)methyl benzoate (143157-27-1)

Guidance literature:

uracil; With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; at 135 - 140 ℃; for 5 - 6h;

2¹-deoxy-2¹,2¹-difluoro-3,5-bis-O-benzoyl-D-ribose trichloroacetimidate; With trimethylsilyl trifluoromethanesulfonate; In acetonitrile;

With water; In dichloromethane; acetonitrile;

upstream raw materials:

2-deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-diphenylmethyl ester-1-methanesulfonate

O,O'-bis-(trimethylsilyl)uracil

(2R,3R)-5-acetoxy-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate

3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-1-O-methanesulfonyl-D-erythro-pentofuranose

Downstream raw materials:

Deoxydifluorouridine

C₃₁H₃₁F₂N₃O₅

Refernces

• 1、 -. "Novel derivatives of nucleosides". . . Retrieved 2017/12/27.
• 2、 -. "SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF". . . Retrieved 2015/04/21.