67814-68-0

Usage

InChI:InChI=1/C8H14O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-7,9-10H,3H2,1-2H3/t4-,5-,6-,7-/m1/s1

Upstream product

• 608-46-8 α-D-lyxopyranose 
• 116-11-0 2-Methoxypropene 
• 87-72-9 D-lyxose 
• 67-64-1 acetone 
• 7306-64-1 2,3,5,6-di-O-isopropylidene-D-mannono-1,4-lactone 
• 1114-34-7 D-lyxose 
• 36468-53-8 β-D-ribofuranose 
• 532-20-7 D-lyxose 
• 77-76-9 2,2-dimethoxy-propane 
• 532-20-7 D-(-)-ribose 
• 50-69-1 D-ribose 
• 10257-32-6 D-ribose 
• 532-20-7 D-Ribose 
• 541546-94-5 allyl α,β-D-ribofuranoside 

Downstream Products

• 123564-95-4 1,5-di-O-(3,5-dinitrophenyl)carbamoyl-2,3-O-isopropylidene-α-D-lyxofuranose 
• 123564-94-3 5-O-(3,5-dinitrophenyl)carbamoyl-2,3-O-isopropylidene-α-D-lyxofuranose 
• 316364-82-6 Toluene-4-sulfonic acid (3aS,4R,6S,6aS)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 138127-49-8 (3aS,6R,6aS)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol 
• 1356163-83-1 (2R,3S,4R,Z)-3,4-O-isopropylidene-1-O-trityl-5-heptadecene-1,2,3,4-tetrol 
• 1356163-80-8 2,3-O-isopropylidene-5-O-trityl-α-D-lyxofuranose 
• 153984-49-7 phenyl 2,3-O-isopropylidene-1-thio-α-D-ribofuranoside 
• 54503-65-0 2,2-dimethyl-6-(trityloxymethyl)tetrahydrofuro[3,4-d][1,3]dioxol-4-ol 
• 1000609-88-0 ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 63029-07-2 methyl 2,3-O-isopropylidene-α-D-lyxofuranoside 
• 1353687-51-0 (4S,5S)-4-((benzyloxy)methyl)-5-ethynyl-2,2-dimethyl-1,3-dioxolane 

Relevant academic research and scientific papers

The first chemical synthesis of pyrazofurin 5′-triphosphate

As an archetype C-nucleoside, pyrazofurin possesses broad-spectrum antiviral and antitumor activities. However, the presence of the acidic enol in the nucleobase of pyrazofurin poses a huge challenge to the conventional NTP synthetic methods. On the basis

Synthetic Study Aiming at the Tricyclic Core of 12- epi-JBIR-23/24

The synthetic study toward highly enantio- and diastereoselective synthesis of the tricyclic framework of 12-epi-JBIR-23/24, a natural product analogue showing inhibitory activity against four malignant pleural mesothelioma cell lines, is presented herein

Synthesis of (2S,3S,4S)-2,3-O-isopropylidene-4-(methoxycarbonylmethyl) cyclopentan-1-one

(2S,3S,4S)-2,3-O-Isopropylidene-4-(methoxycarbonylmethyl)cyclopentan-1-one was synthesized starting from D-ribose through methyl (Z)-3-(5-acetyl-2,2- acetoxyacetyl-2,2-dimethyl-1,3-dioxolan-4-yl)prop-2-enoate which was subjected to cyclization in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene, followed by decarboxylation.

Asymmetric synthesis of (-)-muricatacin's analogue (4S,5R)-5-hydroxy-4- octadecanolide exhibiting the cytotoxicity against esphageal cancer cells

An efficient and facile synthesis, in six steps and 50% overall yield from commercial D-(-)-lyxose as starting material via twice Wittig olefination and one-pot deisopropylidenation and intramolecular lactonization, of the enantiopure (4S,5R)-(+)-5-hydroxy-4-octadecanolide (2), analogue of (-)-muricatacin, and the cytotoxic activity against CE48T cell line (human esophageal carcinoma) are described and the biological activity is the first shown in the literature.

Enantiospecific total synthesis of (?)-crotanecine

Crotanecine is the necine base component of a number of pyrrolizidine alkaloids. This necine subunit is an amino triol bearing a primary allylic alcohol characterized by an all-cis relationship of its stereocenters. The synthesis of crotanecine has been accomplished using simple yet versatile ring construction approach using ribose as chiral starting point.

A highly efficient synthesis of unnatural L-sugars from D-ribose

A preparative and short synthesis of l-ribose and l-apiose was accomplished starting from d-ribose via stereoselective cis-dihydroxylation and C2-hydroxymethylation, respectively. These l-sugars can serve as versatile intermediates for the synthesis of l-nucleosides.

Formal enantioselective synthesis of (-)-carbovir and (-)-abacavir: An application of the rhodium(I)-catalysed tandem hydrosilylation-intramolecular aldol reaction

An efficient synthesis of the highly potent anti-HIV carbocyclic nucleosides (-)-carbovir and (-)-abacavir has been accomplished from D-(-)-ribose using a rhodium(I)-catalysed tandem hydrosilylation-intramolecular aldol strategy to access a key intermediate. Georg Thieme Verlag Stuttgart.

Chiral cyclobutanols and cyclopentane dimers via samarium(II) iodide induced keto-olefin cyclisations of carbohydrate-derived unsaturated ketones

Some pentose and hexose sugars were converted into unsaturated ketone derivatives, which themselves served as substrates for 4-exo-trig radical cyclisation reactions mediated by SmI2. Depending on the order of addition of reagents, the keto-olefins could also be made to undergo a surprising tandem 5-endo-trig cyclisation/dimerisation reaction to a cyclopentane dimer or a cyclobutane monomer. Georg Thieme Verlag Stuttgart.

Efficient and practical synthesis of l-hamamelose

An efficient synthetic route of l-hamamelose was successfully accomplished starting from d-ribose. l-Hamamelose was synthesized in 42% overall yield with six reaction steps via a stereoselective Grignard reaction, a stereoselective crossed aldol reaction

Ten-membered substituted cyclic 2-oxecanone (decalactone) derivatives from Latrunculia corticata, a red sea sponge

Two novel glycosides, latrunculinosides A and B, containing substituted 2-oxecanones (decalactones) were isolated from Latrunculia corticata collected in the Gulf of Aqaba, Israel. They were characterized by spectroscopic methods, predominantly 1H NMR, 13C NMR, MS, IR and UV, and by chemical degradation. Both glycosides contain unusual saccharides such as β-D-olivose, β-L-digitoxose, α-L-amicetose, and β-D-oliose. The compounds gave positive results in antifeeding activity assays. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.