97059-40-0

Basic information

• Product Name: 5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose
• CAS NO: 97059-40-0
• Molecular Weight: 174.197
• Mol File: 97059-40-0.mol

Chemical Properties

• CAS DataBase Reference: 5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose(97059-40-0)
• EPA Substance Registry System: 5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose(97059-40-0)

Safety Data

• Hazardous Substances Data: 97059-40-0(Hazardous Substances Data)

Upstream product

• 4119-18-0 2,2-dimethyl-6-(4-methylphenylsulfonyloxymethyl)-5-(4-methylphenylsulfonyloxymethyl)-(3aR,5R,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxole 
• 4118-63-2 3,5-anhydro-1,2-O-isopropylidene-α-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 55174-91-9 (-)-1,2-O-isopropylidene-5-O-pivaloyl-α-D-xylofuranose 
• 172657-97-5 1,2-O-isopropylidene-α-D-xylofuranose 3,5-O-thionocarbonate 
• 42854-94-4 5-bromo-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 
• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 
• 50600-39-0 5-deoxy-5-iodo-1,2-O-isopropylidene-alpha-D-xylofuranose 
• 24850-33-7 allyltributylstanane 

Downstream Products

• 72933-18-7 (3aR,5R,6S,6aR)-2,2,5-trimethylperhydrofuro[2,3-d][1,3]dioxol-6-yl benzyl ether 
• 926318-90-3 C₃₃H₅₃NO₅Si₂ 
• 926318-78-7 C₁₇H₂₄O₄ 
• 926318-88-9 C₂₁H₂₅NO₅ 
• 926318-87-8 C₂₆H₃₇NO₁₀S 
• 926318-86-7 C₂₅H₃₂O₈ 
• 926318-85-6 C₂₁H₂₄O₆ 
• 926318-96-9 C₂₉H₃₄O₅ 
• 926318-95-8 C₃₂H₃₈O₅ 
• 926318-94-7 C₂₅H₃₂O₅ 
• 926318-83-4 C₂₇H₃₆O₆ 
• 926318-82-3 C₂₀H₃₀O₆ 
• 926318-81-2 C₂₃H₃₄O₅S₂ 
• 926318-80-1 C₂₁H₃₀O₄S₂ 

Relevant articles and documents

Synthesis and in vitro antitumour activity of 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides

A series of novel α-L-threose nucleoside phosphonate analogs, 4(R)-methyl-3-O-phosphonomethyl-α-L-threose nucleosides, were synthesized in multistep sequences starting from D-xylose. The synthetic sequence consisted of the following key stages: (i) the multistep synthesis of 1,2-O-isopropylidenyl-4(R)-methyl-3-O-phosphonomethyl-L-threose, (ii) the transformation of 1,2-O-isopropylidenyl sugar into suitable 1,2-di-O-acyl L-threose precursor, and (iii) the construction of target α-L-threose nucleoside phosphonate analogs by Vorbrüggen glycosidation reaction, deprotection of acyl group, and hydrolysis of diethyl group on phosphonate. The target nucleoside phosphonates were evaluated for their antitumour activities in cell culture-based assays. Compound 8g, 2-fluroadenosine phosphonate, showed remarkable activity against human breast cancer cell lines (MCF-7 and MDA-MB-231) with IC50 values of 0.476 and 0.391 μM, corresponding to 41- and 47-fold higher potency than the reference compound 5-FU, respectively. Subsequent investigations found that the compound 8g can inhibit the proliferation of breast cancer cells and cell cloning. The mechanistic studies indicated that compound 8g could cause DNA damage to breast cancer cells through the ATM-Chk1/Chk2-cdc25c pathway, leading to blockage of the G2/M phase cycle of breast cancer cells, which ultimately led to apoptosis. Moreover, 8g could inhibit the PI3K/AKT signaling pathway and induce apoptosis. These results indicate that compound 8g holds promising potential as an antitumour agent.

Antitumor (4' R)-methyl - α-L . (by machine translation)

The invention discloses novel α-L - fucosa nucleoside phosphonate analogs, and particularly relates to (4 ′). R- Methyl -3 ' - methyl phosphonic acid - α-L . It has the structure shown in Formula 1. Wherein R ' represents H, Na, K or NH. 4 Ions; B stands for uracil, thymine, 5 - chlorouracil, 5 - fluorouracil, 5 -bromouracil, 5 -fluorouracil, cytosine, 5 - fluorocytosine, adenine, 2 - fluoroadenine, 2 - chloroadenine, 2 - aminoadenine and guanine. The compound has anti-tumor activity and good development prospect. (by machine translation)

Synthesis and Antiviral Evaluation of 3'-C-Hydroxymethyl-3'-O-Phosphonomethyl-β-D-5'-deoxyxylose Nucleosides

L-2'-deoxythreose nucleoside phosphonates PMDTA and PMDTT possess potent anti-HIV activity. Herein, a novel class of 3'-C-branched-l-threose nucleoside phosphonate analogs, 5'-deoxy-3'-C-hydroxymethyl-3'-O-phosphonomethyl-d-xylose nucleosides, were synthesized and biologically evaluated. The key sugar intermediate 3-C-benzyloxymethyl-3-O-diethylphosphonomethyl-1,2-O-isopropylidene-α-d-5-deoxyxylose (8) was firstly synthesized, which may be an interesting scaffold for access to diverse 3'-C-branched l-threosyl nucleoside phosphonate derivatives. And the key synthesis involved Wittig olefination of 1,2-O-isopropylidene-3-oxo-α-d-5-deoxyxylose, stereoselective dihydroxylation of alkenes by aqueous KMnO4, selective benzylation of hydroxymethyl group under activation of dibutyltin oxide, and introduction of phosphonate group by nucleophilic substitution. Eventually, glycosylation under Vorbrüggen conditions provided 3'-C-hydroxymethyl-3'-O-phosphonomethyl-β-d-5'-deoxyxylose nucleoside analogs in satisfying yield.

Palladium-catalyzed enantioselective allylic substitution in the presence of monodentate furanoside phosphoramidites

A library of monodentate furanoside phosphoramidites, easily synthesized from inexpensive D-xylose and optically pure 1,1-bi-2-naphthol (BINOL), was used as ligands for the palladium-catalyzed allylic alkylation and amination. The matched pair was formed from D-xylose-derivatives and (S)-BINOL. The asymmetric induction depends strongly on the substituent at the C5 of the carbohydrate backbone; both bulky 5-O-pivaloyl and 5-deoxy derivatives gave excellent results, whereas ligands with trityl protection at position C5 induced low ee values with reversal of configuration. The solvent used for the addition is also of great importance with highest enantioselectivities observed in diethyl ether. The best results for both alkylation and amination, up to 98-99 ee, were obtained for sterically demanding allylic acetates. Single is better: New carbohydrate ligands bearing a single 1,1-bi-2-naphthol (BINOL)-derived phosphoramidite moiety are developed and successfully applied to the palladium-catalyzed asymmetric allylic substitution. The enantioselectivities are equal or better than those obtained for similar systems containing two BINOL moieties and reach up to 99 ee.

Generation of a low-valent titanium species from titanatrane and its catalytic reactions: Radical ring opening of oxetanes

Treatment of a titanatrane complex with trimethylsilyl chloride and magnesium powder in tetrahydrofuran generated a low-valent titanium species. This species catalyzed the radical ring opening of epoxides and oxetanes to produce the corresponding less substituted alcohols. The reagent also catalyzed the deallylation and depropargylation of allylic and propargylic ethers, respectively, to provide the parent alcohols.

Batch to flow deoxygenation using visible light photoredox catalysis

Herein we report a one-pot deoxygenation protocol for primary and secondary alcohols developed via the combination of the Garegg-Samuelsson reaction, visible light-photoredox catalysis, and flow chemistry. This procedure is characterized by mild reaction conditions, easy-to-handle reactants and reagents, excellent functional group tolerance, and good yields.

Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions

Radical reactions are a powerful class of chemical transformations. However, the formation of radical species to initiate these reactions has often required the use of stoichiometric amounts of toxic reagents, such as tributyltin hydride. Recently, the use of visible-light-mediated photoredox catalysis to generate radical species has become popular, but the scope of these radical precursors has been limited. Here, we describe the identification of reaction conditions under which photocatalysts such as fac-Ir(ppy) 3 can be utilized to form radicals from unactivated alkyl, alkenyl and aryl iodides. The generated radicals undergo reduction via hydrogen atom abstraction or reductive cyclization. The reaction protocol utilizes only inexpensive reagents, occurs under mild reaction conditions, and shows exceptional functional group tolerance. Reaction efficiency is maintained upon scale-up and decreased catalyst loading, and the reaction time can be significantly shortened when the reaction is performed in a flow reactor.

First total synthesis of a naturally occurring iodinated 5′-deoxyxylofuranosyl marine nucleoside

4-Amino-7-(5′-deoxy-β-D-xylofuranosyl)-5-iodo-pyrrolo[2,3-d] pyrimidine 1, an unusual naturally occurring marine nucleoside isolated from an ascidan, Diplosoma sp., was synthesized from D-xylose in seven steps with 28% overall yield on 10 g scale. The key step was Vorbrueggen glycosylation of 5-iodo-pyrrolo[2,3-d]pyrimidine with 5-deoxy-1, 2-O-diacetyl-3-O-benzoyl-D- xylofuranose. Its absolute configuration was confirmed.

NOVEL DERIVATIVES OF ACYL CYANOPYRROLIDINES

A compound of formula (I) or a tautomeric form, regioisomer, stereoisomer, solvate, N-oxide or pharmaceutically acceptable salts thereof; wherein 'a' - is selected from the group consisting of substituted or unsubstituted heterocycloalkyl ring and substituted or unsubstituted carbohydrate moiety y is a member selected from -O-, -CO-, -S02-, aminoalkyl or formula (II) wherein, Rw is hydrogen, substituted or unsubstituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl; x is a member selected from -0-, -S-, -SO-, -S02-, CONR10, NR10CO and -NRd-, or x and y together represent a chemical bond; Z is selected from -CH-, -N-. t is an integer selected from O to 4; with the provisos that when 'a' is substituted or unsubstituted heterocycloalkyl ring then 't' is not O and when y = -CO-, x is not NRd.

Processes for the preparation of (R)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol"

The present invention provides various processes for the preparation of (R)-±-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol. These processes may be characterized by the following scheme: