65247-32-7

Upstream product

• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 87-72-9 L-(+)-arabinose 
• 7473-38-3 benzyl β-L-arabinopyranoside 
• 100-51-6 benzyl alcohol 
• 7296-55-1 L-arabinose 
• 250224-22-7 (3R,4S,5S)-2-Benzyloxy-tetrahydro-pyran-3,4,5-triol 
• 245729-74-2 benzyl 3,4-O-isopropylidene arabinoside 
• 7296-56-2 β-L-arabinopyranose 

Downstream Products

• 118533-11-2 benzyl 2-deoxy-3,4-O-isopropylidene-2C<(E)-methoxycarbonylmethylene>-β-L-erythro-pentopyranoside 
• 118533-09-8 benzyl 2-deoxy-3,4-O-isopropylidene-2C<(Z)-methoxycarbonylmethylene>-β-L-erythro-pentopyranoside 
• 87598-87-6 benzyl 3,4-O-(1-methylethylidene)-2-C-methyl-β-L-arabinopyranoside 
• 26685-74-5 1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose 
• 123490-19-7 benzyl 2-deoxy-3,4-O-isopropylidene-2-methylene-β-L-erythro-pentopyranoside 
• 582310-82-5 benzyl-3,4-O-isopropylidene-2-C-trifluoromethyl-β-L-ribopyranoside 
• 118533-10-1 (7S,7aR)-4-Benzyloxy-7-hydroxy-7,7a-dihydro-4H,6H-furo[3,2-c]pyran-2-one 
• 118533-09-8 [(3aS,7aR)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-(7E)-ylidene]-acetic acid methyl ester 
• 118533-09-8 [(3aS,7aR)-6-Benzyloxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-(7E)-ylidene]-acetic acid methyl ester 
• 123516-55-2 C₁₇H₂₀Cl₂O₄ 
• 123490-26-6 Acetic acid (7S,8R)-7-acetoxy-4-benzyloxy-5-oxa-spiro[2.5]oct-8-yl ester 
• 123490-20-0 C₁₇H₂₀O₄ 
• 123490-22-2 C₁₇H₂₁ClO₄ 
• 123490-23-3 C₁₇H₂₂O₄ 

Relevant academic research and scientific papers

Synthesis of 6- and 7-(1,2,3-trihydroxy-1,2-O-isopropyl-denepropyl)pteridines and deoxygenation of their 3′-hydroxy groups

Treatment of 3,4-O-isopropylidene-L-threo-pentos-2-ulose (7) with 5,6-diamino-1,3-dimethyluracil (8) afforded 1,3-dimethyl-6-[(1R,2S)-1,2,3-trihydroxy-1,2-O-isopropylidenepropyl]lumazine (9a) and its 7-substituted isomer (9b). Deoxygenation of 3′-hydroxy

A solid-phase approach to novel purine and nucleoside analogs

This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbrueggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective oxidation-reduction procedure of the 2-OH group. Some compounds exhibited moderate activity against HIV-1 in PBM cells.

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).

Efficient synthesis of 2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) from L-arabinose

An efficient and practical route for the large-scale synthesis of 2-deoxy-L-erythro-pentose (2-deoxy-L-ribose) starting from L-arabinose was developed using Barton-type free-radical deoxygenation reaction as a key step. The radical precursor, a phenoxythi

A bioisosteric oligosaccharide mimetic based on isofagomine-type monomers

A series of hydroxylated piperidine oligomers that resemble oligosaccharides is synthesised. Prepared were 5, a mimic of 3-O-L-fucopyranosyl-D-galactopyranose, 6, a mimic of 3-O-D-galactopyranosyl-D-galactopyranose and 7, a mimic of 3-O-{3-O-[3-O-(L-fucop

A practical synthesis of L-FMAU from L-arabinose

A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-β-L- arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L- Arabinose was convened to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-β-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.

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.

A CONCISE SYNTHESIS OF PATULIN FROM ARABINOSE

Conversion of arabinose (5) to the protected ketone (7), followed by Wittig condensation to (9), acid catalysed cyclisation (to 10), and dehydration, provides a brief synthesis of the fungal metabolite patulin (1), produced by Penicillium and Aspergilius

Chiral Multifunctional Isoprene Units by Ring-Contraction of Riboside Oxiranes

Lithium bromide induced ring-contraction of benzyl 2,3- and 3,4-anhydro-β-D(and L)-ribopyranoside (1 and 4) in HMPA/toluene or tetramethylurea (TMU)/toluene gave (R)(and S)-2-(benzyloxy)-2,5-dihydrofufan-4-carboxaldehyde (2 and 5) together with a small amount of benzyl 4-bromo-4-deoxy-β-L(and D)-lyxopyranoside (3 and 6).The latter compound was formed with lithium bromide in 1,1,1-trichloroethane.Benzyl 2,3- and 3,4-anhydro-2-deuterio-β-L-ribopyranoside (4d and 8d) gave the deuterated aldehyde 5d, which carried a vinylic deuterium atom, wheraes benzyl 2,3-anhydro-4-deuterio-β-L-ribopyranoside (4d' ) gave the nondeuterated aldehyde 5.On the basis of these experiments, the mechanism of the ring-contraction as postulated.