117249-16-8

Usage

Chemical Properties

white crystalline powder

InChI:InChI=1/C13H16O3/c1-10-13(12(14)7-8-15-10)16-9-11-5-3-2-4-6-11/h2-8,10,12-14H,9H2,1H3/t10-,12-,13-/m0/s1

Upstream product

• 100-39-0 benzyl bromide 
• 53657-42-4 L-rhamnal 
• 149561-65-9 (-)-(2S,3S)-3-(Benzyloxy)-2-methyl-2,3-dihydro-4H-pyran-4-one 
• 101856-96-6 (2S,3S,4S)-4-(tert-butyldimethylsilyloxy)-3,4-dihydro-3-hydroxy-2-methyl-2H-pyran 
• 293736-30-8 3-O-(tert-butyldimethylsilyl)oxy-4-O-benzyl-L-rhamnal 
• 69980-52-5 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 
• 294202-29-2 (2S,3S,4S)-3-(benzyloxy)-2-methyl-3,4-dihydro-2H-pyran-4-yl acetate 
• 34819-86-8 3,4-di-O-acetyl-6-deoxy-L-glucal 
• 117249-17-9 3,4-di-O-benzyl-L-rhamnal 

Downstream Products

• 1615710-95-6 3-O-[4-O-benzyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl]-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol 
• 106988-72-1 3-O-Acetyl-1,5-anhydro-4-O-benzyl-2,6-didesoxy-L-ribo-hex-1-enit 
• 149561-65-9 (-)-(2S,3S)-3-(Benzyloxy)-2-methyl-2,3-dihydro-4H-pyran-4-one 
• 106988-70-9 1,5-Anhydro-4-O-benzyl-2,6-dideoxy-L-ribo-hex-1-enitol 
• 1615710-96-7 3-O-[4-O-benzyl-2,3,6-trideoxy-β-L-erythro-hex-2-enopyranosyl]-1,5-anhydro-4-O-benzyl-2,6-dideoxy-L-arabino-hex-1-enitol 

Relevant academic research and scientific papers

Synthesis of the bis(cyclohexenone) core of (-)-lomaiviticin A

(-)-Lomaiviticin A is a complex C2-symmetric bacterial metabolite comprising two diazotetrahydrobenzo[b]fluorene (diazofluorene) residues and four 2,6-dideoxy glycosides, α-l-oleandrose and N,N-dimethyl-β-l-pyrrolosamine. The two halves of lomaiviticin A are linked by a single carbon-carbon bond oriented syn with respect to the oleandrose residues. While many advances toward the synthesis of lomaiviticin A have been reported, including synthesis of the aglycon, a route to the bis(cyclohexenone) core bearing any of the carbohydrate residues has not been disclosed. Here we describe a short route to a core structure of lomaiviticin A bearing two α-l-oleandrose residues. The synthetic route features a Stille coupling to form the conjoining carbon-carbon bond of the target and a double reductive transposition to establish the correct stereochemistry at this bond. Two synthetic routes were developed to elaborate the reductive transposition product to the bis(cyclohexenone) target. The more efficient pathway features an interrupted Barton vinyl iodide synthesis followed by oxidative elimination of iodide to efficiently establish the enone functionalities in the target. The bis(cyclohexenone) product may find use in a synthesis of lomaiviticin A itself.

Synthesis of the α-Linked Digitoxose Trisaccharide Fragment of Kijanimicin: An Unexpected Application of Glycosyl Sulfonates

Previously, we demonstrated that glycosyl tosylates are effective for the synthesis of β-glycosides of gluco-configured 2-deoxy sugars. Here, we show the same sulfonate system can be used for the selective synthesis of α-glycosides containing the allo-con

Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks

An automated continuous flow system capable of producing protected deoxy-sugar donors from commercial material is described. Four 2,6-dideoxy and two 3-amino-2,3,6-trideoxy sugars with orthogonal protecting groups were synthesized in 11–32 % overall yields in 74–131.5 minutes of total reaction time. Several of the reactions were able to be concatenated into a continuous process, avoiding the need for chromatographic purification of intermediates. The modular nature of the experimental setup allowed for reaction streams to be split into different lines for the parallel synthesis of multiple donors. Further, the continuous flow processes were fully automated and described through the design of an open-source Python-controlled automation platform.

Modular continuous flow synthesis of orthogonally protected 6-deoxy glucose glycals

An efficient, modular continuous flow process towards accessing two orthogonally protected glycals is described with the development of reaction conditions for several common protecting group additions in flow, including the addition of benzyl, naphthylme

MACROCYCLIC PICOLINAMIDE COMPOUNDS WITH FUNGICIDAL ACTIVITY

This disclosure relates to macrocyclic picolinamides of Formula (I) and their use as fungicides.

MACROCYCLIC PICOLINAMIDES AS FUNGICIDES

The invention relates to macrocyclic picolinamides of Formula I and their use as fungicides.

Methods and compositions for the manufacture of C-3' and C-4' anthracycline antibiotics

The present invention discloses new and novel substituted anthracyclines with modified alkyl-aromatic ring substitutions on the C-3′ of the sugar moiety or modified or unmodified alkyl-aromatic ring substitutions at the C-4′ of the sugar moiety. It also d

Simple oxidation of 3-O-silylated glycals: Application in deblocking 3-0-protected glycals

A high yielding allylic oxidation of 3-O-siIylated glycals 5-10 with the reagent system PhI(OAc)2-TMSN3 is presented. The iodine(m) species generated under these conditions is a lot more effective for generating carbohydrate-derived 3-trialkylsiloxy-2,3-d

SELECTIVER AUFBAU α-L-(1->4)-VERKNUEPFTER 2,6-DIDESOXY-OLIGOSACCHARIDE

The phase-transfer catalyzed benzylation of 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (L-rhamnal, 5) led to a mixture of 4- and 3-O-benzyl derivatives in the ratio of 2:1.By silylation, 5 was regiospecifically transformed into either the 3-O-tert-but