18933-65-8

Upstream product

• 6752-48-3 methyl 2-deoxy-4,6-O-benzylidene-α-D-ribo-hexopyranoside 
• 21090-92-6 methyl-[O⁴,O⁶-((R)-benzylidene)-O³-methyl-α-D-ribo-2-deoxy-hexopyranoside] 
• 126373-46-4 4,6-O-Benzylidene-2-deoxy-3-O-methyl-α-D-arabino-hexopyranoside 
• 6752-48-3 methyl 4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 
• 160400-66-8 methyl 2-deoxy-D-arabinopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 63598-31-2 methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose 

Downstream Products

• 1393730-58-9 4-O-acetyl-D-cymaropyranosyl ortho-hexynylbenzoate 
• 1393730-49-8 methyl 4-O-(2,4-di-O-benzoyl-D-thevetopyranosyl)-β-D-cymaropyranoside 
• 1393730-48-7 methyl 4-O-(2,4-di-O-benzoyl-D-thevetopyranosyl)-α-D-cymaropyranoside 
• 4166-79-4 methyl 2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside 
• 61653-43-8 Benzoic acid (2R,3R,4S,6S)-4,6-dimethoxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 148944-21-2 Methyl 6-azido-4-O-benzoyl-2,6-dideoxy-3-O-methyl-α-D-ribo-hexopyranoside 

Relevant academic research and scientific papers

Total syntheses of the non-peptide bradykinin B1 receptor antagonist velutinol a and its analogs, seco-pregnanes with a cage-like moiety

We describe here the syntheses of velutinol A (1) and the structurally similar compounds 24 sharing a highly oxygenated seco-pregnane cage-like structure. The synthesis of velutinol A (1, 15,16-seco-pregnane) features the highly regioselective construction of |14 silyl enol ether from 15-keto-21,22-diol, followed by stereoselective introduction of a sterically hindered β-hydroxy group at the C14 position by Rubottom oxidation. Prolonged reaction time and the use of an excess amount of mCPBA at this step allowed double Rubottom oxidation, enabling us to introduce the requisite hydroxy groups at the C14 and C16 positions in one pot. Subsequent oxidative cleavage of the C1516 bond, deprotection, and intramolecular acetalization allowed the concise total synthesis of velutinol A (1). Utilization of α,α-dihydroxy-ketone, the double Rubottom oxidation product, for formation of the ether F-ring by 5-exo-cyclization, and subsequent C1421 oxidative cleavage, effectively achieved the synthesis of pentalinonside-aglycon (2). Construction of the 14,15-seco-structures of two other analogs, argeloside aglycon (3) and illustrol (4), was achieved by BaeyerVilliger oxidation of 15(21)-keto derivatives. Introduction of the 20-oxo group potentially embedded in argeloside aglycon was accomplished by Wacker oxidation of |20, which was constructed by GriecoNishizawa syn-β-elimination of the C21-primary alcohol obtained by reduction of the BaeyerVilliger product. Intra-molecular double acetalization of the 15,16-dihydroxy-14,20-oxo derivative to form the cage-like structure of the DEF-rings required a moderately weak acid. This step was the key to accessing argeloside aglycon (3), as otherwise the easily aromatized β,γ-dihydroxyketone moiety was transformed to furan. Sharpless asymmetric dihydroxylation of |20 to set the C20 stereocenter, followed by intramolecular double acetalization, achieved the stereoselective synthesis of illustrol With all synthesized compounds, structural requirements of steroidal bradykinine B1 receptor antagonist would be revealed.

Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity

Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.

Expeditious synthesis of saponin P57, an appetite suppressant from Hoodia plants

Pregnane glycoside P57, the appetite suppressant component from Hoodia, was synthesized expeditiously, featuring preparation of the aglycone Hoodigogenin A from digoxin and assembly of the deoxytrisaccharide with glycosyl o-alkynylbenzoates as donors.