4096-62-2

Upstream product

• 87-72-9 L-(+)-arabinose 
• 91-09-8 methyl β-L-arabinopyranoside 
• 6960-39-0 methyl 3,4-O-isopropylidene-β-L-arabinopyranoside 
• 7296-56-2 β-L-arabinopyranose 

Downstream Products

• 24558-73-4 Methyl-3,4-O-isopropyliden-β-L-ribosid 
• 817620-70-5 (3aS,6S,7aR)-6-Methoxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 4421-83-4 methyl 3,4-O-isopropylidene-2-O-p-tolylsulfonyl-β-L-ribopyranoside 
• 90987-05-6 methyl 3-benzamido-2-O-benzoyl-3,4-dideoxy-α-D-erythro-pentopyranoside 
• 55898-24-3 methyl 3,4-dideoxy-3-salicylideneamino-α-D-erythro-pentopyranoside 
• 55898-23-2 methyl 4-deoxy-α-D-glycero-pentopyranosid-3-ulose phenylhydrazone 
• 91-09-8 methyl β-L-arabinopyranoside 
• 87-72-9 L-ribose 
• 90986-99-5 methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosidulose syn-phenylhydrazone 
• 90986-99-5 methyl 3,4-O-isopropylidene-β-L-erythro-pentopyranosidulose anti-phenylhydrazone 
• 55898-21-0 3,4-O-isopropylidene-L-erythro-pentosazone 
• 55898-19-6 2S-methoxytetrahydropyran-3,4-dione 4-phenylhydrazone 

Relevant academic research and scientific papers

Catalytic asymmetric epoxidation of alkenes with arabinose-derived uloses

Four L-erythro-2-uloses were readily prepared from L-arabinose via a reaction sequence involving Fischer glycosidation, acetalization and oxidation. Bulky steric sensors at the anomeric center could enhance the stereoselectivity of the dioxirane epoxidation and one of the uloses performed with good enantioselectivity towards trans-stilbene (up to 90% ee). However, the catalysts decomposed during the epoxidation and the maximum chemical yield was only 13% under the basic conditions. Three L-threo-3-uloses could overcome the decomposition problem based on the electron withdrawing effect of the ester group(s) α to the ketone functionality. The best chemical yield was up to 93% using a ketone with two flanking ester groups. One of the improved uloses displayed moderate enantioselectivity towards trans-disubstituted and trisubstituted alkenes (40-68% ee).

A practical synthesis of L-ribose

L-Ribose was synthesized by a simple four-step method with overall yield of 76.3% from a protected L-arabinose derivative, which is a compatible intermediate for the synthesis of L-deoxyribose. The key step of this strategy is the Swern oxidation and subsequent stereoselective reduction accompanied by inversion of the 2-hydroxy group of protected L-arabinose.

Synthesis of 13C-Labeled Patulin [4-Hydroxy-4H-furo[3,2-c]pyran-2(6H)-one] to Be Used as Internal Standard in a Stable Isotope Dilution Assay

A synthetic route was established for the preparation of [13C2]-4-hydroxy-4H-furo[3,2-c]pyran-2(6H)-one (patulin) to be used in a stable isotope dilution assay. Mass spectral analyses were performed using electron impact ionization (EI), negative electrospray ionization (ESI), collision-induced dissociation (CID), and atmospheric pressure ionization. Fragmentation routes in the EI mode and in CID were concluded and compared with each other.

Ylidenebutenolide Mycotoxins. Concise Syntheses of Patulin and Neopatulin from Carbohydrate Precursors

Conversion of arabinose 10 to the protected ketone 13 followed by Wittig condensation to 14, acidcatalysed cyclisation (to lactone 16), dehydration and deprotection provides a brief synthesis of the mycotoxic substance patulin 1, which is produced by Penicillium and Aspergillus spp.In a similar manner, the biogenetic precursor to patulin, neopatulin 8, is synthesized from lyxose 25 via the key intermediates 24, 28 and 30.