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

Chemical Properties

Crystalline Solid

Uses

1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose is a versatile carbohydrate derivative univerisally used for the preparation of 2 deoxynucleosides.

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

• 452-51-7 D-2-deoxyribose 
• 874-60-2 4-methyl-benzoyl chloride 
• 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 

Downstream Products

• 50908-41-3 2,5-anhydro-3-deoxy-4,6-di-O-toluoyl-D-ribohexononitrile 
• 50908-40-2 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythropentofuranosyl 1-cyanide 
• 87008-95-5 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)pyridazin-6-one 
• 87008-96-6 3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-α-D-erythro-pentofuranosyl)pyridazin-6-one 
• 80585-28-0 C₂₉H₃₀N₄O₆ 
• 80083-17-6 4-(3,5-di-O-p-toluoyl-2-deoxy-β-D-erythro-pentofuranosyl)-6-methyl-1,2,4-triazin-3(4H)-one 1-oxide 
• 80083-18-7 4-(3,5-di-O-p-toluoyl-2-deoxy-α-D-erythro-pentofuranosyl)-6-methyl-1,2,4-triazin-3(4H)-one 1-oxide 
• 80585-28-0 3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-ethyl-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one 
• 80595-97-7 3-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)-5-ethyl-6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one 
• 95936-30-4 1-(2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranosyl)-4-methylimidazole-5-carboxamide 
• 95936-32-6 1-(2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranosyl)-5-methylimidazole-4-carboxamide 
• 108008-59-9 1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-5-(2-fluoroethyl)-1H,3H-pyrimidine-2,4-dione 
• 108008-60-2 1-(2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl)-5-(2-fluoroethyl)-1H,3H-pyrimidine-2,4-dione 
• 156270-71-2 5-(2-thienyl)-1-(2'-deoxy-3',5'-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-6-azauracyl 

Relevant articles and documents

Benzimidazole derivative BI292 as well as preparation method and application thereof

The invention discloses a benzimidazole derivative BI292 and a preparation method thereof, and the benzimidazole derivative BI292 is chemically named as 1-[(2R, 4S, 5R)-4-hydroxy-5-(hydroxymethyl) tetrahydrofuran-2-yl]-1H-benzo [d] imidazole-4-carboxylic acid methyl ester. The benzimidazole derivative and the pharmaceutically acceptable salt, the solvate and the hydrate of the benzimidazole derivative have excellent in-vivo and in-vitro anti-tumor activity on MCF-7, SK-BR-3, HCT 116, U-118 MG, U-87 MG and MDA-MB-468, and have a relatively 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.