92131-91-4

Usage

Uses

Used in Pharmaceutical Industry:
1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate is used as a key intermediate in the synthesis of novel tetrahydropyran-based dipeptide isosters, which are further utilized in the development of topoisomerase inhibitors. These inhibitors have potential applications in the treatment of various diseases, including cancer and bacterial infections.
Used in Carbohydrate Chemistry:
1,5-Anhydro-2,3-dideoxy-D-erythro-hex-2-enitol 4,6-Diacetate is also used in the synthesis of D-allosamine derivatives, which are important building blocks in carbohydrate chemistry. These derivatives can be employed in the development of glycoconjugates, glycoproteins, and other complex carbohydrate structures with potential applications in drug discovery and vaccine development.

Upstream product

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

Downstream Products

• 850753-00-3 4,6-di-O-benzyl-1,5-anhydro-D-erythrohex-2-enitol 
• 1387444-05-4 1,5-anhydro-2,3-dideoxy-4-O-diphenylphosphino-6-O-trityl-D-erythro-hex-2-enitol 
• 125878-19-5 4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyric acid (2R,3S)-2-((E)-2-benzyloxycarbonyl-vinyl)-tetrahydro-pyran-3-yl ester 
• 125878-22-0 (E)-4-{(2R,3S)-3-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-butyryloxy]-tetrahydro-pyran-2-yl}-but-2-enoic acid benzyl ester 
• 125878-16-2 (E)-4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-but-2-enoic acid (2R,3S)-2-benzyloxycarbonylmethyl-tetrahydro-pyran-3-yl ester 
• 125877-88-5 benzyl (E)-3-<(2R,3S)-3-<(E)-3-<(2S,3R)-3-(benzyloxy)-3,4,5,6-tetrahydro-2H-pyran-2-yl>propenyloxy>-3,4,5,6-tetrahydro-2H-pyran-2-yl>propenoate 
• 125878-14-0 3-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-propionic acid (2R,3S)-2-benzyloxycarbonylmethyl-tetrahydro-pyran-3-yl ester 
• 125878-11-7 {(2R,3S)-3-[2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-acetoxy]-tetrahydro-pyran-2-yl}-acetic acid benzyl ester 
• 125877-86-3 benzyl (E)-3-<(2R,3S)-3-(tert-butyldimethylsiloxy)-3,4,5,6-tetrahydro-2H-pyran-2-yl>propenoate 
• 125878-03-7 (E)-4-[(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-but-2-enoic acid benzyl ester 
• 125878-00-4 [(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-acetic acid benzyl ester 
• 125877-87-4 benzyl (E)-3-<(2R,3S)-3-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-yl>propenoate 
• 125878-04-8 (E)-4-((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-but-2-enoic acid benzyl ester 
• 125878-01-5 ((2R,3S)-3-Hydroxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester 

Relevant academic research and scientific papers

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.

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.

TETRAHYDRO-IMIDAZO QUINOLINE COMPOSITIONS AS CBP/P300 INHIBITORS

The present disclosure is directed to inhibitors of the CBP/p300 family of bromodomains. The compounds can be useful in the treatment of disease or disorders associated with the inhibition of the CBP/p300 family of bromodomains. For instance, the disclosure is concerned with compounds and compositions for inhibition of the CBP/p300 family of bromodomains, methods of treating, preventing, or ameliorating diseases or disorders associated with the inhibition of CBP/p300 family of bromodomains, and methods of synthesis of these compounds.

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- And S-linked glycosides

A convenient protocol was developed for the synthesis of 2,3-unsaturated C-, O-, N- and S-linked glycosides (enosides) using 20 mol % perflurophenylboronic acid catalyst via Ferrier rearrangement. Using this protocol, D-glucals and L-rhamnals reacted with various C-, O-, N- and S-nucleophiles to give a wide range of glycosides in up to 98% yields with mainly α-anomeric selectivity. The perflurophenylboronic acid successfully catalyzed a wide range of substrates (both glucals and nucleophiles) under very mild reaction conditions.

Substrate specificity of tuliposide-converting enzyme, a unique non-ester-hydrolyzing carboxylesterase in tulip: Effects of the alcohol moiety of substrate on the enzyme activity

6-Tuliposides A (PosA) and B (PosB) are glucose esters accumulated in tulip (Tulipa gesneriana) as major defensive secondary metabolites. Pos-converting enzymes (TgTCEs), which we discovered previously from tulip, catalyze the conversion reactions of PosA

Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity

Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator that specifically activates membrane proteins of the P2Y and its related families of G protein-coupled receptors (GPCR), GPR34 (LPS1), P2Y10 (LPS2), and GPR174 (LPS3). Here, in order to increase potency and receptor selectivity, we designed and synthesized LysoPS analogues containing the conformational constraints of the glycerol moiety. These reduced structural flexibility by fixation of the glycerol framework of LysoPS using a 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton, and related structures identified compounds which exhibited high potency and selectivity for activation of GPR34 or P2Y10. Morphing of the structural shape of the 2-hydroxymethyl-3-hydroxytetrahydropyran skeleton into a planar benzene ring enhanced the P2Y10 activation potentcy rather than the GPR34 activation.

A mild and efficient Zn-catalyzed C-glycosylation: Synthesis of C(2)-C(3) unsaturated C-linked glycopyranosides

A highly efficient C-glycosylation method was developed by using catalytic Zn(OTf)2 for the synthesis of 2,3-unsaturated C-glycosides. The scope of the protocol was well illustrated with different substituted glycals and nucleophiles comprising