3601-89-6

Basic information

• Product Name: 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose
• Synonyms: 2-DEOXY-3,5-DI-O-P-TOLUOYL-RIBOFURANOSYL CHLORIDE;1-CHLORO-3',5'-DI-O-TOLUOYL-2-DEOXYRIBOSIDE;1-(ALPHA)-CHLORO-3,5-DI-O-(P-TOLUOYL)-2-DEOXY-D-RIBOSE;2-Deoxy-3,5-Di-O-P-Toluoyl-D-Ribofuranosyl Chloride;1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose;3,5-Di-O-(p-toluyl)-2-deoxy-D-ribofuranosyl chloride;2-Deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranosyl Chloride;3,5-Di-O-p-toluoyl-2-deoxy-D-ribofuranosyl Chloride
• CAS NO: 3601-89-6
• Molecular Formula: C₂₁H₂₁ClO₅
• Molecular Weight: 388.85
• EINECS: 2017-001-1
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 3601-89-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 109°C dec.
• Boiling Point: 518.4 °C at 760 mmHg
• Flash Point: 185.6 °C
• Appearance: Crystalline solid
• Density: 1.283 g/cm³
• Refractive Index: 1.581
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Dichloromethane (Slightly), DMSO
• CAS DataBase Reference: 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose(3601-89-6)
• EPA Substance Registry System: 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose(3601-89-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 3601-89-6(Hazardous Substances Data)

Usage

Description

1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose is a crystalline solid that is a versatile carbohydrate derivative. It is widely utilized in the preparation of 2-deoxynucleosides, which are essential components in various chemical and biological applications.

Uses

Used in Pharmaceutical Industry:
1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose is used as a key intermediate for the synthesis of 2-deoxynucleosides, which are crucial in the development of antiviral and anticancer drugs. Its role in the pharmaceutical industry is to facilitate the creation of life-saving medications by providing a stable and reliable starting material for the production of these therapeutic agents.
Used in Chemical Research:
In the field of chemical research, 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose is used as a valuable compound for studying the properties and reactions of carbohydrates. Its unique structure allows researchers to explore various chemical modifications and interactions, contributing to the advancement of carbohydrate chemistry and related fields.
Used in Biochemical Applications:
1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose is also employed in biochemical applications, where it serves as a building block for the synthesis of complex carbohydrates and glycoconjugates. These molecules play a vital role in various biological processes, including cell signaling, immune response, and protein folding. The use of this compound in biochemical research aids in understanding the fundamental aspects of these processes and their implications in health and disease.

InChI:InChI=1/C21H21ClO6/c1-13-7-3-5-9-15(13)20(23)25-12-18-17(11-19(26-18)28-22)27-21(24)16-10-6-4-8-14(16)2/h3-10,17-19H,11-12H2,1-2H3/t17-,18+,19?/m0/s1

Synthetic route

5-aminothaizolo<4,5-d>pyrimidine-2,7(3H,6H)-dione (30161-97-8) + 1-chloro-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose (3601-89-6) → 5-amino-3-(2-deoxy-3,5-di-O-toluoyl-D-erythro-pentofuranosyl)thiazolo<4,5-d>pyrimidine-2,7-dione (124737-27-5, 135505-31-6)

Conditions	Yield
With trimethylsilyl fluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane 1.) reflux, 3 h, 2.) 110 deg C, 30 min; Yield given. Multistep reaction;

1-chloro-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose (3601-89-6) → 5-amino-3-(2-deoxy-β-D-erythro-pentofuranosyl)thiazolo<4,5-d>pyrimidine-2,7-dione (124737-22-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) trimethylsilyl fluoromethanesulfonate, hexamethyldisilazane (HMDS) / 1.) reflux, 3 h, 2.) 110 deg C, 30 min 2: 42 percent / NaOMe / methanol / 8 h / Ambient temperature View Scheme

Upstream product

• 51255-17-5 1-O-methyl-2-deoxy-D-ribofuranoside 
• 22900-10-3 2-deoxy-D-ribose 
• 4330-34-1 methyl 3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 452-51-7 D-2-deoxyribose 
• 874-60-2 4-methyl-benzoyl chloride 

Downstream Products

• 114184-61-1 4-(2-deoxy-3,5-di-O-p-tolyl-β-D-erythro-pentofuranosyl)-5-methyl-1,4-thiazine-3-one 
• 4330-24-9 (furan-2-yl)methyl 4-methylbenzoate 
• 79378-88-4 4-Amino-8-<2-desoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-rinofuranosyl>-7(8H)-pteridinon 
• 79378-90-8 4-<2-Desoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-ribofuranosylamino>-7(8H)-pteridinon 
• 79395-76-9 4-Amino-8-<2-desoxy-3,5-bis-O-(4-methylbenzoyl)-α-D-ribofuranosyl>-2-phenyl-7(8H)-pteridinon 
• 79063-65-3 C₂₉H₂₆N₂O₇ 
• 79063-63-1 C₂₉H₂₆N₂O₇ 
• 132163-37-2 5-benzyl-2'-deoxy-3',5'-bis(O-p-toluoyl)uridine 
• 132163-38-3 5-benzyl-1-(2-deoxy-3,5-bis(O-p-toluoyl)-α-D-ribofuranosyl)uracil 
• 124737-27-5 5-amino-3-(2-deoxy-3,5-di-O-toluoyl-D-erythro-pentofuranosyl)thiazolo<4,5-d>pyrimidine-2,7-dione 
• 163020-54-0 2-(3,5-dichloroanilino)-6-chloro-9-(2-deoxy-3,5-di-p-tolyl-β-D-ribofuranosyl)purine 
• 192570-37-9 1-(3,5-di-O-p-toluoyl-2-deoxy-α,β-D-erythro-pentofuranosyl)-5-chloro-quinazoline-2,4(3H)-dione 
• 192570-36-8 1-(3,5-di-O-p-toluoyl-2-deoxy-α,β-D-erythro-pentofuranosyl)-5-fluoro-quinazoline-2,4(3H)-dione 
• 272460-76-1 C₂₉H₃₀O₅ 

Relevant articles and documents

Benzimidazole derivative BI305 and preparation method and application thereof

The invention discloses a benzimidazole derivative BI305 and a preparation method thereof, and the chemical name of the benzimidazole derivative BI305 is 1-[tetrahydro-4-hydroxy-5-(hydroxymethyl) furan-2-yl]-N, N-dimethyl-1H-benzo [d] imidazole-4-formamide. The benzimidazole derivative and the pharmaceutically acceptable salt, solvate and hydrate thereof have excellent anti-tumor in-vivo and in-vitro activity on MCF-7, SK-BR-3, HCT 116, U-118 MG, U-87 MG and MDA-MB-468, and have a good application prospect in preparation of anti-tumor drugs.

Introduction of peptide functions into DNA by nucleic acid peptides, NAPs

Nucleic acid peptides (NAPs) with a mimetic amino acid side residue at the base position of the nucleotide via an amide bond were synthesized from 3-deoxy-6-O-(4,4′-dimethoxytrityl)allonic acid methyl ester as the common precursor. Furthermore, an NAP with an octapeptide at the C1′ position was synthesized. The peptide-linked NAP exhibits both functions of the oligopeptide part and of the oligonucleotide part. Copyright

Convenient preparation of 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

By using acetyl chloride as HCl generator, the procedure for the Hoffer preparation of the α-chloro sugar 4a was significantly improved. The α-configuration of the chloro atom was confirmed by using NOE measurement. Sequential transformation of 4a to the β-anomer and to the furfuryl derivative 6 was studied.