141846-57-3

Usage

Uses

Used in Organic Synthesis:
ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) is used as a synthetic intermediate for the development of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex molecules, such as pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) is used as a key component in the synthesis of novel drug candidates. Its chemical properties enable the development of new molecules with potential therapeutic applications, contributing to the advancement of drug discovery and innovation.
Used in Chemical Research:
ALPHA-L-ERYTHRO-PENTOFURANOSYL CHLORIDE-2-DEOXY-BIS(4-METHYL BENZOATE) is also used as a research tool in chemical laboratories. Its unique structure and reactivity make it an interesting subject for studying various chemical reactions and mechanisms, which can lead to a better understanding of organic chemistry and the development of new synthetic strategies.

InChI:InChI=1/C21H21ClO5/c1-13-3-7-15(8-4-13)20(23)25-12-18-17(11-19(22)26-18)27-21(24)16-9-5-14(2)6-10-16/h3-10,17-19H,11-12H2,1-2H3/t17?,18-,19+/m0/s1

Upstream product

• 452-51-7 D-2-deoxyribose 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 212499-77-9 2-deoxy-1,3,5-tri-O-p-toluoyl-β-L-erythro-pentofuranose 
• 364042-57-9 4-cyano-4-deoxy-1,2-O-isopropylidene-D-erythritol 
• 874-60-2 4-methyl-benzoyl chloride 
• 38996-14-4 (4R,5S)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 38996-09-7 5-bromo-2,5-dideoxy-D-threo-pentono-1,4-lactone 
• 82805-10-5 2,5-dibromo-2,5-dideoxy-D-lyxono-1,4-lactone 
• 15384-37-9 D-xylono-1,4-lactone 
• 87-72-9 D-Xylose 
• 817621-14-0 C₂₉H₂₈O₇ 
• 22837-36-1 methyl-2-deoxy-3,5-di-O-p-toluoyl-α-L-erythropentofuranoside 
• 446251-73-6 (2S,3R)-2-(hydroxymethyl)-5-methoxytetrahydrofuran-3-ol 
• 532-20-7 L-arabinose 

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

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.

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.

Tibifudine process for the preparation of key intermediate

The invention discloses a new technology for preparation of telbivudine important intermediate Hoffer's chlorosugar, the new technology is characterized in that: using a known compound (R)-3-(S)-2, 2-dimethyl-1, 3-dioxolame-4-yl)-3-hydroxy propanenitrile (compound 2) as a starting material to obtain the target compound Hoffer's chlorosugar, namely 1-chloro-3, 5-di-O-p-toluene formyl-2-deoxy-L-ribose by hydroxyl protection, reducing, ring opening under acidic conditions, aldol condensation, then chlorination and other steps, the total yield of the line is 42%, and the product purity is greater than 98.8%.

Development of a novel synthetic process for 2-deoxy-3,5-di-O-p-toluoyl- α-L-ribofuranosyl chloride: A versatile intermediate in the synthesis of 2′-deoxy-L-ribonucleosides

A novel synthetic route to 2-deoxy-3,5-di-O-p-toluoyl-α-L- ribofuranosyl chloride (1) from inexpensive D-xylose (3) is described. 1 is a key intermediate in the synthesis of the antiviral agent 1-(2-deoxy-β-L- ribofuranosyl)thymine (β-L-thymidine) (2) and

Synthesis of beta-L-2'-deoxy nucleosides

An improved process for the preparation of 2′-modified nucleosides and 2′-deoxy-nucleosides, such as, β-L-2′-deoxy-thymidine (LdT), is provided. In particular, the improved process is directed to the synthesis of a 2′-deoxynucleoside that may utilize different starting materials but that proceeds via a chloro-sugar intermediate or via a 2,2′-anhydro-1-furanosyl-nucleobase intermediate. Where an 2,2′-anhydro-1-furanosyl base intermediate is utilized, a reducing agent, such as Red-Al, and a sequestering agent, such as 15-crown-5 ether, that cause an intramolecular displacement reaction and formation of the desired nucleoside product in good yields are employed. An alternative process of the present invention utilizes a 2,2′-anhydro-1-furanosyl base intermediate without a sequestering agent to afford 2′-deoxynucleosides in good yields. The compounds made according to the present invention may be used as intermediates in the preparation of other nucleoside analogues, or may be used directly as antiviral and/or antineoplastic agents.

PROCESS FOR THE PREPARATION OF 1-CHLORO-3,5-DI-O-ACYL-2-DEOXY-L-RIBOFURANOSIDE DERIVATIVES

Herein described is a process for the preparation of 1-chloro-3,5-di-O-acyl-2-deoxy-L-ribofuranoside derivatives of general formula (I) useful as intermediates in processes for preparing nucleotides of the L series having antiviral activity.

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

Methods of manufacture of 2'-deoxy-beta-L-nucleosides

The present invention relates to the synthesis of 2′-deoxy-β-L-thymidine, 2′-deoxy-β-L-uridine and 2′-deoxy-β-L-cytidine, and their derivatives, such as the 3′-O-acyl or 3′,5′-O-diacyl prodrugs, including the 3′-O-L-aminoacyl and 3′,5′-O-L-diaminoacyl prodrugs, and particularly the 3′-O-L-valinyl and 3′,5′-O-L-divalinyl prodrugs.

Efficient synthesis of 2-deoxy L-ribose from L-arabinose: mechanistic information on the 1,2-acyloxy shift in alkyl radicals.

[formula: see text] Conversion of the inexpensive L-arabinose 1 into the ethylthio ortho ester 7 followed by generation of the dialkoxyalkyl radical III produces the desired 2-deoxy-L-ribose triester 4 in excellent overall yield. It has been shown that th