85846-80-6

Usage

Uses

Used in Organic Synthesis:
(3aR,6R,6aR)-6-(benzyloxyMethyl)-2,2-diMethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one is used as a reagent or intermediate for the preparation of other compounds in the field of organic synthesis. Its unique molecular structure, including the benzyloxyMethyl group and dioxolane ring, makes it a potentially valuable component in the creation of various organic molecules.

Upstream product

• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 100-39-0 benzyl bromide 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 5336-08-3 D-Ribono-1,4-lactone 
• 93-99-2 benzoic acid phenyl ester 
• 157453-65-1 (3R,4S,5R)-5-(tert-butyldimethylsilyloxymethyl)-3,4-dihydroxy-dihydrofuran-2-one 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 78508-91-5 5-benzyloxy-2-hydroxy-3-hydroxy-D-ribonolactone 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 117251-95-3 Dimethyl (6-O-benzyl-3,4-O-isopropylidene-α-D-ribo-2-hexulofuranosyl)phosphonate 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 
• 198969-39-0 5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose 
• 106839-88-7 2-Benzyloxy-1-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol 
• 160584-05-4 1-O-Acetyl-5-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-β-D-ribofuranose 
• 160584-04-3 1-O-Acetyl-5-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-α-D-ribofuranose 
• 117251-95-3 Dimethyl (6-O-benzyl-1-deoxy-3,4-O-isopropylidene-β-D-ribo-hex-2-ulofuranosyl)phosphonate 
• 582313-73-3 2-(6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)propionic acide ethyl ester 
• 582313-74-4 2-(6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)propionic-1-ol 
• 582313-75-5 4-[2-(6-benzyloxymethyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)propoxy]benzaldehyde 
• 130607-26-0 [5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione 
• 129744-45-2 [5S-(5α,7α,8β,9β)]-7-(benzyloxymethyl)-8,9-isopropylidenedioxy-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione 
• 133908-91-5 [5R-(5α,7β,8α,9α)]-7-(benzyloxymethyl)-1,3-diaza-8,9-isopropylidenedioxy-6-oxaspiro[4.4]nonane-2,4-dione 
• 339540-27-1 methyl 2,5-anhydro-6-O-benzyl-2-chloro-2-deoxy-3,4-O-isopropylidene-α-D-ribo-hexofuranosonate 

Relevant academic research and scientific papers

Highly regioselective and stereoselective synthesis of C-Aryl glycosidesvianickel-catalyzedortho-C-H glycosylation of 8-aminoquinoline benzamides

C-Aryl glycosides are of high value as drug candidates. Here a novel and cost-effective nickel catalyzedortho-CAr-H glycosylation reaction with high regioselectivity and excellent α-selectivity is described. This method shows great functional group compatibility with various glycosides, showing its synthetic potential. Mechanistic studies indicate that C-H activation could be the rate-determining step.

High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues

A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.

NUCLEOTIDE AND NUCLEOSIDE THERAPEUTIC COMPOSITIONS AND USES RELATED THERETO

This disclosure relates to nucleotide and nucleoside therapeutic compositions and uses in treating infectious diseases, viral infections, and cancer, where the base of the nucleotide or nucleoside contains at least one thiol, thione or thioether.

Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals

The fragmentation of primary alkoxyl radicals is usually a minor process with respect to hydrogen abstraction and other competing reactions. However, when β-amino alcohols were used as substrates, the scission proceeded in good to excellent yields and no side reactions were observed. The fragmentation can be coupled with an allylation or alkylation reaction, to give alkaloid analogues and functionalized nitrogen heterocycles. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Ophthamological drugs

The present invention relates generally to ophthamological drugs. More specifically, the inventon relates to a method of modifying (derivatizing) ophthamological drugs so as to increase their penetration through the cornea. The invention also relates to d

Syntheses of hydantocidin and C-2-thioxohydantocidin

Hydantocidin (12), a naturally occurring strong herbicide, was synthesized in 35.2% overall yield, with accompanying 5-epi-hydantocidin (12′) in 9.6% overall yield via isothiocyanate (13) and spiro-hydantoin (10) from 2,3-O-isopropylidene-D-ribono-1,4-lactone (1). C-2-Thioxo-hydantocidin (24) was also synthesized in 16.5% overall yield with accompanying 5-epi-C-2-thioxohydantocidin (24′, 9.2% yield) via isothiocyanate (22).

Synthesis of hydantocidin and C-2-thioxo-hydantocidin

Hydantocidin, a naturally occurring strong herbicide, was synthesized in an overall yield of 35.2%, with the accompanying 1′-epi-hydantocidin in overall 9.6% yield from 2,3-O-isopropylidene-D-ribono-1,4-lactone. C-2-thioxo-hydantocidin and its spiro-epimer were also synthesized in an overall yield of 14.4% and 8.5%, respectively.

A ring closing metathesis-osmylation approach to oxygenated oxepanes as carbohydrate surrogates

A ring closing metathesis (RCM)-osmylation sequence has been developed for the formation of highly oxygenated cyclic ethers from the corresponding acyclic dienes. A systematic examination of various substrates in this reaction revealed that the process is general in scope and is insensitive to the number of alkoxy substituents present. Subsequent osmylation of the metathesis product proceeds with excellent diastereoselectivity to furnish highly oxygenated oxepanes. These oxepanes represent one-carbon homologated carbohydrates.

Titanocene-Catalyzed Reduction of Lactones to Lactols

A convenient method for the conversion of lactones to lactols is described. The hydrosilylation to lactols is carried out via air-stable titanocene difluoride or a titanocene diphenoxide precatalyst using inexpensive polymethylhydrosiloxane (PMHS) as the stoichiometric reductant. These procedures have been demonstrated with a variety of substrates and proceed in good to excellent yield.

2-PHENYL-1,3-BENZODITHIOLYLIUM TRIFLUOROMETHANESULFONATE: A REAGENT FOR THE CONVERSION OF ALCOHOLS INTO BENZYL ETHERS AND BENZOATES UNDER MILD CONDITIONS.

2-Phenyl-1,3-benzodithiolylium trifluoromethanesulfonate, easily prepared from 1,2-benzenedithiol, converts alcohols into dithioorthoesters and ultimately, benzyl ethers (Bu3SnH) and benzoates (HgO/HBF4).