149342-25-6

Upstream product

• 92131-90-3 ((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 
• 109-63-7 trifluoroborane diethyl ether 
• 2873-29-2 D-glucal triacetate 
• 617-86-7 triethylsilane 
• 76223-29-5 4'-methoxyphenyl 4,6-di-O-acetyl-2,3-dideoxy-1-O-α-D-erythro-hex-2-enopyranoside 
• 3323-72-6 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 

Downstream Products

• 850753-00-3 4,6-di-O-benzyl-1,5-anhydro-D-erythrohex-2-enitol 
• 176738-51-5 Toluene-4-sulfonic acid (2R,3S)-3-methanesulfonylmethoxy-tetrahydro-pyran-2-ylmethyl ester 
• 176738-40-2 Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester 
• 176738-55-9 Toluene-4-sulfonic acid 2-((2R,3S)-3-but-3-enyloxy-tetrahydro-pyran-2-yl)-ethyl ester 
• 176738-52-6 toluene-4-sulfonic acid (2'R,3'S)-3'-but-3-enylxytetrahydropyran-2'-ylmethyl ester 
• 176738-50-4 Toluene-4-sulfonic acid (2R,3S)-3-methylsulfanylmethoxy-tetrahydro-pyran-2-ylmethyl ester 
• 176738-39-9 toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester 
• 176738-53-7 (2'R,3'S)-(3'-but-3-enyloxytetrahydropyran-2'-yl)acetonitrile 
• 161946-35-6 toluene-4-sulfonic acid (2'R,3'S)-3'-hydroxytetrahydropyran-2'-ylmethyl ester 
• 234087-18-4 Acetic acid (2R,5R)-3-hydroxy-5-phenyl-tetrahydro-pyran-2-ylmethyl ester 
• 234087-16-2 (2R,5R)-2-Hydroxymethyl-5-phenyl-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

First example of the activation of polymethylhydrosiloxane with molecular iodine: A facile synthesis of 3,6-dihydropyran derivatives

Glycals react rapidly with polymethylhydrosiloxane (PMHS) in the presence of a catalytic amount of molecular iodine under mild conditions to afford the corresponding 3,6-dihydropyran derivatives in excellent yields. Et 3SiH/I2 was al

Efficient carbon-Ferrier rearrangement on glycals mediated by ceric ammonium nitrate: Application to the synthesis of 2-deoxy-2-amino-C-glycoside

A carbon-Ferrier rearrangement on glycals has been performed by using ceric ammonium nitrate to obtain products in moderate to good yields with high selectivity. The versatility of this method has been demonstrated by applying it to differently protected

Microwave-induced, InCl3-catalyzed Ferrier rearrangement of acetylglycals: Synthesis of 2,3-unsaturated C-glycosides

Indium(III) chloride-catalyzed, microwave-assisted Ferrier rearrangement of different per-O-acetylglycals leads to an efficient synthesis of 2,3-unsaturated C-glycosides in good to excellent yields.

Synthesis of 2,3-unsaturated C-glycosides by HClO4-SiO 2 catalyzed Ferrier rearrangement of glycals

Alkyl 2,3-unsaturated C-glycopyranosides have been prepared by Ferrier rearrangement of acyl or alkyl protected glycals catalyzed by HClO 4-SiO2.

Expeditious diastereoselective synthesis of medium ring heterocycle-fused chromenes via tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition

The first examples of highly diastereoselective tandem 8/9-endo-dig and 8-exo-dig hydroalkoxylation-formal-[4 + 2] cycloaddition are described for the synthesis of medium ring heterocycle-fused chromenes. TMS-alkynols preferred the exo-dig mode of hydroalkoxylation over the endo-dig mode leading to spiro-cyclic chromenes. The method could be used for the synthesis of linearly-fused ladder-like polyethers. A thia-heterocycle-fused chromene could be transformed into a complex bridged tricyclic ketal by a tandem carbene-insertion-[2,3]-sigmatropic shift.

ZrCl4-catalyzed efficient ferrier glycosylation: A facile synthesis of pseudoglycals

The reaction of tri-O-acetyl-D-glucal with silyl nucleophiles, alcohols and thiols was effectively promoted by a catalytic amount of zirconium(IV) chloride to produce the corresponding pseudoglycals via Ferrier rearrangement.

Synthesis and anticancer activity of triazole linked macrocycles and heterocycles

Synthesis of macrocylic enones starting from alkyl ether and triazole as a linker was achieved using click reaction and intramolecular aldol condensation. The newly synthesized macrocyclic enone was successfully utilized as a dipolarophile in 1,3-dipolar

Regio- And diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides

An efficient regio- and diastereoselective arylation method of readily available 2,3-glycals with various aryl iodides has been established. Using the Pd(OAc)2/AsPh3 precatalytic system, this protocol proved to be general to prepare a variety of substituted C2-aryl glycosides in good yields with complete diastereoselectivity.

Synthesis and biological evaluation of novel pyrane glycosides

A series of novel (5R)-5-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-(4-fluorophenyl)-2,6-diphenyl-3,3a,5,6-tetrahydro-2H-pyrazolo[3,4-d]thiazoles 11a–g and (5R)-5-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-(4-fluorophenyl)-6-phe-nyl-3,3a,5,6-tetrahydroisoxazolo[3,4-d]thiazoles 12a–g were synthesized by the reaction of chalcone derivatives of (R,Z)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-5-(4-fluorobenzylidene)-3-phenylthiazolidin-4-ones 10a–g with phenylhydrazine and hydroxylamine hydrochloride. The chemical structures of newly synthesized compounds were elucidated by IR, NMR, MS and elemental analysis. The compounds 11a–g and 12a–g were evaluated for their antibacterial activity and antifungal activity.

Microwave-assisted synthesis and anticancer activity of triazolyl thiazolidine derivatives of pyrene

In a one pot procedure a series of (R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-3-phenylthiazolidin-4-ones 9a–g and 2-((2R)-2-((2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-yl)-4-oxo-3-phenylthiazolidin-5-yl)acetic acids 10a–g was prepared by condensation of (2S,3S)-3-((1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl)methoxy)-3,6-dihydro-2H-pyran-2-carbaldehyde with mercapto acids and primary amines in the presence of ZnCl2 under both microwave irradiation and conventional heating conditions. Characterization of new compounds has been done by means of IR, NMR, MS and elemental analysis. The cytotoxicity was assessed against a panel of four different human tumor cell lines: A549 derived from human alveolar adenocarcinoma epithelial cells (ATCC No. CCL-185), Hela derived from human cervical cancer cells (ATCC No. CCL-2), MDA-MB-231 derived from human breast adenocarcinoma cells (ATCC No. HTB22) and HEK 293 (normal human embryonic kidney cell line) using the MTT assays. Among the tested compounds 9e and 10e showed the most potent activity against MCF-7 breast cancer cell line with IC50 values of 1.91 and 1.95 μΜ, whereas 9b, 10b, 9g and 10g showed promising activity against MDA-MB-231 and Hela cell lines with IC50 values of 5.84, 5.74, 7.89 and 7.65 μΜ, respectively.