3601-89-6

Usage

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 1-Chloro-3,5-di-O-toluoyl-2-deoxy-D-ribofuranose 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

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

Downstream Products

• 16727-51-8 1-(2,6-bis-benzyloxy-pyridin-3-yl)-ξ-D-erythro-1,2-dideoxy-pentofuranose 
• 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 

Relevant academic research and scientific papers

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.

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.

Synthesis of (2-deoxy-α- and -β-D-erythro-pentofuranosyl)(thymin-1-yl)alkanes and their incorporation into oligodeoxyribonucleotides. Effect of nucleobase-sugar linker flexibility on the formation of DNA-DNA and DNA-RNA hybrids

On the basis of modeling studies, the (2-deoxy-α- and β-D-erythro-pentofuranosyl) (thymin-1-yl) alkanes 1a,b and 2a,b were selected as potential conformational probes for altDNA oligonucleotides. A straightforward approach to the synthesis of 1a,b and 2a,b from commercial 2-deoxy-D-ribose (3) and 1-O-methyl-2-deoxy-3,5-di-0-p-toluoyl-D-erythro-pentofuranose (13), respectively, was developed. These nucleoside analogues were converted to the phosphoramidite derivatives 27a,b-30a,b and incorporated into oligonucleotide 31 at predetermined sites and defined internucleotidic motifs. The insertion of 1a,b according to either a (3′ → 5′)- or a (3′ → 3′)-internucleotidic polarity produced oligonucleotides exhibiting a slightly higher affinity for their complementary unmodified DNA sequence than for the corresponding RNA sequence (Table 3). Conversely, the incorporation of 2a into 31 according to a (3′ → 3′)-orientation generated, for the first time, an altDNA oligonucleotide displaying a greater affinity for its complementary unmodified RNA sequence (ΔTm = 6°C) than for the corresponding DNA sequence (ΔTm = 10°C). This hybrid was, however, thermodynamically less stable than the duplex having unmodified α-2′-deoxythymidine similarly incorporated into 31 (ΔΔTm = 3°C).

[(2-deoxy-α- and β-D-erythro-pentofuranosyl)thymin-1-yl] methane derivatives as potential conformational probes for altDNA oligonucleotides

The previously unknown deoxyribonucleoside analogues 2a,b have been efficiently synthesized from commercial 1-O-methyl-2-deoxy-3,5-di-O-p-toluoyl-D-erythro-pentofuranose. The conversion of these nucleosides to the phosphoramidite derivatives 13a,b and 14a,b for subsequent incorporation into oligodeoxyribonucleotide analogues is also described.

Novel DNA Analog for Potential Gene Regulating Agent. A Convenient Synthesis of α-Oligodeoxyribonucleotide Phosphorothioate Bearing 3'-Monophosphate

α-2'-Deoxyoctathymydilic acid phosphorothioate analog bearing 3'-monophosphate was conveniently synthesized via phosphoramidite method using a riboadenosine attached Teflon-based solid support.The obtained oligomer exhibited enhanced stability toward the digestion by common nucleases.