1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose

Base Information

• Chemical Name: 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose
• CAS No.: 21740-23-8
• Molecular Formula: C19H15Cl3O5
• Molecular Weight: 429.684
• European Community (EC) Number: 606-827-9
• NSC Number: 140594
• DSSTox Substance ID: DTXSID40944353
• Mol file: 21740-23-8.mol

Synonyms:21740-23-8;1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose;2-deoxy-3,5-di-O-(4-chlorobenzoyl)-alpha-D-ribofuranosyl chloride;NSC140594;1-Chloro-3,5-di-(p-chlorobenzoyl)-2-deoxy-D-ribofuranose;SCHEMBL6406571;DTXSID40944353;3,5-bis-o-(4-chlorobenzoyl)-2-deoxypentofuranosyl chloride;MFCD11044532;AKOS015963291;NSC-140594;SY226329;FT-0656487;A815720;3,5-BIS[O-(P-CHLORBENZOYL)]-.ALPHA.-D-RIBOFURANOSYLCHLORIDE;[5-chloranyl-3-(4-chlorophenyl)carbonyloxy-oxolan-2-yl]methyl 4-chloranylbenzoate;4-chlorobenzoic acid [5-chloro-3-[(4-chlorophenyl)-oxomethoxy]-2-oxolanyl]methyl ester

Chemical Property of 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.5E-19mmHg at 25°C
• Melting Point: 110-118 °C (dec.)
• Refractive Index: 1.636
• Boiling Point: 530.6 °C at 760 mmHg
• Flash Point: 193 °C
• PSA: 61.83000
• Density: 1.46 g/cm³
• LogP: 4.72960
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 427.998507
• Heavy Atom Count: 27
• Complexity: 516

Purity/Quality:

99% ^*data from raw suppliers

3,5-Di-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1Cl)COC(=O)C2=CC=C(C=C2)Cl)OC(=O)C3=CC=C(C=C3)Cl
• Uses: Intermediate used in the synthesis of nucleotide analogs.Unstable in solution! 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose is used in the synthesis of nucleotide analogs. Unstable in solution!

Technology Process of 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose

There total 5 articles about 1-Chloro-3,5-di-(4-chlorobenzoyl)-2-deoxy-D-ribose 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: 82.0%

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) + 4-chloro-benzoyl chloride (122-01-0) → 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (21740-23-8)

Guidance literature:

D-2-deoxyribose; With methanol; acetyl chloride; at 25 ℃; for 0.75h;

4-chloro-benzoyl chloride; With pyridine; dmap; at 0 - 25 ℃;

With hydrogenchloride; In diethyl ether; acetic acid; at 0 ℃; for 0.166667h;

DOI:10.1081/NCN-100001435

Reference yield: 77.0%

methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside (80339-59-9) → 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (21740-23-8)

Guidance literature:

With hydrogenchloride; acetic acid; acetyl chloride; In 1,4-dioxane; chloroform; at 13 - 15 ℃; Inert atmosphere;

Reference yield:

4-chloro-benzoyl chloride (122-01-0) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → 3,5-O-bis(4-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl chloride (21740-23-8)

Guidance literature:

4-chloro-benzoyl chloride; 1-O-methyl-2-deoxy-D-ribofuranoside; With triethylamine; dmap; In 1,4-dioxane; at 15 - 18 ℃;

With hydrogenchloride; acetic acid; acetyl chloride; In 1,4-dioxane; at 12 - 18 ℃;

upstream raw materials:

D-2-deoxyribose

4-chloro-benzoyl chloride

1-O-methyl-2-deoxy-D-ribofuranoside

methyl 3,5-dibenzoyloxy-2-deoxy-α-D-erythropentofuranoside

Downstream raw materials:

C₃₁H₂₃Cl₂N₅O₆

C₃₇H₂₇Cl₂N₅O₆

4-Amino-2-phenyl-8-[2-deoxy-3,5-di-O-(4-chlorobenzoyl)-β-D-ribofuranosyl]-pteridine-7-one

C₃₄H₂₈Cl₂N₆O₆

Refernces

• 1、 Wang,Duan,Wiebe,Balzarini,De Clercq,Knaus. "Synthesis of 1-(2-deoxy-β-D-ribofuranosyl)-2,4-difluoro-5- substituted-benzene thymidine mimics, some related α-anomers, and their evaluation as antiviral and anticancer agents". . p. 11 - 40. Retrieved 2007/10/03.
• 2、 -. "Process for Producing 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-trifluoromethyluracil Derivatives". . . Retrieved 2008/06/13.