19877-13-5

Usage

Chemical compound

A substance with a specific molecular structure that is formed by a chemical reaction.

Complex molecular structure

The compound has a complex arrangement of atoms and functional groups.

Contains isopropylidene, benzyloxy, and dideoxy functional groups

These functional groups give the compound its unique properties and reactivity.

Derivative of glucopyranose

Glucopyranose is a type of sugar, and the compound is derived from it.

Used in organic chemistry synthesis

The compound is used as a building block for more complex molecules in organic chemistry.

Building block for complex molecules

The compound can be used to create more complex molecules with potential applications.

Potential applications in the pharmaceutical industry

The compound has potential uses in the development of new drugs.

Development of antiviral and antimicrobial agents

The compound may be used to create new drugs that fight viruses and bacteria.

Unique structure and reactivity

The compound's structure and reactivity make it a valuable tool for creating novel chemical compounds.

Creation of novel chemical compounds with potential therapeutic properties

The compound can be used to create new compounds that may have therapeutic benefits.

InChI:InChI=1/C16H20O4/c1-4-12-13(17-10-11-8-6-5-7-9-11)14-15(18-12)20-16(2,3)19-14/h4-9,12-15H,1,10H2,2-3H3/t12-,13+,14?,15?/m1/s1

Upstream product

• 127666-20-0 3-O-benzyl-6-deoxy-6-iodo-1,2-O-isopropylidene-5-O-(diphenylphosphinyl)-α-D-glucofuranose 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 308290-81-5 C₁₅H₁₈O₅ 
• 18439-45-7 3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose 
• 18439-45-7 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-C-methyl-β-L-ido-pentofuranose 
• 190733-40-5 (3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-((R)-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-tetrahydro-furo[2,3-d][1,3]dioxole 
• 158946-12-4 3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose 
• 74152-53-7 O¹,O²-isopropylidene-O³-methanesulfonyl-α-D-xylo-5,6-dideoxy-hex-5-enofuranose 
• 100-39-0 benzyl bromide 
• 7284-07-3 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-eno-furanose 
• 120368-01-6 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulphonyl-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 

Downstream Products

• 30361-13-8 (4S)-O³-benzyl-O¹,O²-isopropylidene-4-[(Ξ)-3-(4-nitro-phenyl)-4,5-dihydro-isoxazol-5-yl]-β-L-threofuranose 
• 204057-85-2 (3aR,5S,6R,6aR)-6-Benzyloxy-5-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-1-iodo-decyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole 
• 204057-92-1 (3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-octyl)-tetrahydro-furo[2,3-d][1,3]dioxole 
• 204057-84-1 (3aR,5S,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluoro-1-iodo-octyl)-tetrahydro-furo[2,3-d][1,3]dioxole 
• 39798-94-2 (2S,3R,4R,5R)-4-Benzyloxy-5-vinyl-tetrahydro-furan-2,3-diol 
• 37776-17-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 35781-78-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 41670-98-8 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-xylo-hept-6-enofuranos-5-ulose 
• 76801-66-6 5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexodialdo-1,4-furanose 
• 1373283-23-8 2-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-1,4-furanosyl)-2,3-dihydro-4H-pyran-4-one 
• 1373283-21-6 2-(3-O-benzyl-1,2-O-isopropylidene-5-deoxy-α-D-xylo-1,4-furanosyl)-2,3-dihydro-4H-pyran-4-one 

Relevant academic research and scientific papers

The nitrile oxide/isoxazoline approach to eleven-carbon monosaccharides: cycloaddition of D- and L-arabinonitrile oxides to 5,6-dideoxyhex-5-enofuranoses and characterisation of the resulting 2-isoxazolines

Cycloaddition of 2,3:4,5-di-O-isopropylidene-D-arabinonitrile oxide 5, generated by base-induced dehydrochlorination of hydroximoyl chloride 10, to D-Glc-derived alkene 7 afforded an 89:11 diastereomeric mixture of (5R)- and (5S)-3-(1,2:3,4-di-O-isopropyl

Construction of key building blocks towards the synthesis of cortistatins

This work reports the construction of key building blocks towards the synthesis of cortistatins; a family of steroidal alkaloids. Cortistatin A, being a primary target due to its superior biological properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from d-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A.

A stereoselective approach for the total synthesis of (-)-tadanalactam from acetonide-d-glucose

A stereoselective and realistic approach for the total synthesis of naturally occurring δ-lactam (-)-tadanalactam, has been accomplished from the commercially existing acetonide-d-glucose involving Birch reduction, Pinnick oxidation, Staudinger reaction,

Synthesis of a furanosyl-pyranone derivative related to the tri-o-heterocyclic core of herbicidins

A new compound that is structurally related to the undecose ring structure of herbicidins has been prepared. The synthesis of this novel furanosyl-pyranone derivative was made possible through the regioselective reductive ring-opening of a 3,5-O-benzylidene-D-xylofuranose and the hetero-Diels-Alder reaction of an aldehyde and a Danishefsky-type diene. The highly functionalized pyranone derivative can be a useful precursor for the synthesis of herbicidins.

Studies on the synthesis of the C-glycosidic part of nogalamycin, part 1

Studies aimed at the construction of the C-glycosidic part of nogalamycin (1) and menogarol (2) are described. The stereochemistry of the addition of aryl lithiums to 4-acetyl-1,3-dioxolane 16, prepared from D-glucose via 10a-15, was studied. The major isomers were the (S)-isomers 17a and 17b as shown by X-ray analysis of 17a with the unnatural configuration. The adduct 17a was further converted to the anomeric naphthoquinones 22a and 22b by acetal cleavage, ozonolysis, acetalization and Diels-Alder reaction with 1-methoxybutadiene.

Applications of Cyclic Sulfates of vic-Diols: Synthesis of Episulfides, Olefins, and Thio Sugars

A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of inc-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to ep

Synthesis of Sugar Episulfides and Olefins from vic-Diols via Cyclic Sulfates

Cyclic sulfates of vic-diols are transformed in one-pot into sugar episulfides by treatment with potassium thioacetate or thiourea followed by reaction with sodium methoxide; reaction of these cyclic sulfates with potassium selenocyanate followed by treat

Fluorination Reactions at C-5 of 3-O-Benzyl-6-deoxy-1,2-isopropylidenehexofuranoses

Fluorination reactions of 2-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-gluco-, β-L-ido-, α-D-allo-, and β-L-talo-furanoses (1, 2, 3, and 4) were investigated.The reaction of 1 with diethylaminosulfur trifluoride (DAST) predominantly produced 2-O-benzyl-5,6-dideoxy-5-fluoro-1,2-O-isopropylidene-α-D-glucofuranose with the retention of the configuration at C-5.Both of the fluorides with retained and inverted configurations were obtained in the fluorination of 2 with DAST.In contrast, only the inversion of the configuration occurred when 3 and 4 were reacted with DAST.The reactions of the methanesulfonates of 3 and 4 with tetrabutylammonium fluoride (TBAF) and those of their trifluoromethanesulfonates with tris(dimethylamino)sulfonium difluorotrimethylsilicate (TASF) gave the 5-deoxy-5-fluoro derivatives with the inversion of each configuration and the 5,6-unsaturated derivative.However, the reactions of the sulfonates of 1 and 2 overwhelmingly produced the 4,5- and 5,6-eliminated derivatives.For the reaction in which the steric hindrance of the benzyloxyl group at C-3 and the electronic repulsion of ring oxygen to the SN2 displacement with fluoride anion are significant, such as the fluorination of 1 with DAST, the SNi mechanism is reasonable.

Sugar Vinyltin Derivatives - Stable Precursors of Sugar Carbanions

Sugar acetylenes 4a-4f were treated with tri-n-butyltin hydride at 140o in the presence of AIBN.Acetylenes 4a-4e were easily converted into cis vinyltin derivatives 5a-5e which isomerized under these conditions to the more stable trans isomers

Formation and structures of (E)- and (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofu ranoses

The reactions of 3-O-benzyl-6-deoxy-1,2-O-isopropylidene-5-O-methanesulfonyl-α-D-gluco - and β-L-idofuranoses (1 and 2) with tetrabutylammonium fluoride in N,N-dimethylformamide gave (E)- and (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-β-L-threo-hex-4