377075-27-9

Upstream product

• 28697-53-2 D-arabinopyranose 
• 98-88-4 benzoyl chloride 
• 10323-20-3 D-Arabinose 

Downstream Products

• 905918-00-5 2,3,4-tri-O-benzoyl-D-arabinopyranosyl bromide 
• 61134-26-7 benzyl α-D-arabinopyranoside 
• 61134-28-9 benzyl 2-O-p-tosyl-α-D-arabinopyranoside 
• 76825-34-8 benzyl 3,4-O-isopropylidene-α-D-arabinopyranoside 
• 61134-27-8 1-O-Benzyl-3,4-O-isopropyliden-2-O-(p-toluolsulfonyl)-D-arabinosid 
• 61134-24-5 Benzyl 2,3-anhydro-α-D-ribopyranoside 
• 186697-05-2 benzyl 2,3,4-tri-O-benzoyl-α-D-arabinopyranoside 
• 1022935-02-9 C₂₆H₂₂O₈ 
• 40010-17-1 2,3,4-tri-O-benzoyl-β-D-arabinopyranosyl bromide 

Relevant academic research and scientific papers

TRITERPENES DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS OR ANTI-INFLAMMATORY AGENTS

A compound of formula (1): wherein R1 is selected from the group consisting of H, α-L-Rhamnopyranose, α-D-Mannopyranose, β-D-Xylopyranose, β-D-Glucopyranose, and α-D-Arabinopyranose; R2 is selected from CH3, COOH, CH2OH, COOCH3 and CH2O-α-D-Arabinopyranose; with the proviso that the compound of formula (I) is not a compound of formula (I) wherein R1 is β-D-Glucopyranose and R2 is COOH; wherein R1 is α-L-Rhamnopyranose and R2 is CH3; wherein R1 is β-D-Glucopyranose and R2 is CH2OH; wherein R1 is β-D-Xylopyranose and R2 is CH2OH; wherein R1 is α-L-Rhamnopyranose and R2 is COOCH3, wherein R1 is H and R2 is CH3; wherein R1 is H and R2 is CH2OH; wherein R1 is H and R2 is COOH; or wherein R1 is H and R2 is COOCH3, or a pharmaceutically acceptable salt thereof.

Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents

The weak hydrosolubility of betulinic acid (3) hampers the clinical development of this natural anticancer agent. In order to circumvent this problem and to enhance the pharmacological properties of betulinic acid (3) and the lupane-type triterpenes lupeol (1), betulin (2), and methyl betulinate (7), glycosides (β-d-glucosides, α-l-rhamnosides, and α-d-arabinosides) were synthesized and in vitro tested for cytotoxicity against three cancerous (A-549, DLD-1, and B16-F1) and one healthy (WS1) cell lines. The addition of a sugar moiety at the C-3 or C-28 position of betulin (2) resulted in a loss of cytotoxicity. In contrast, the 3-O-β-d-glucosidation of lupeol (1) improved the activity by 7- to 12-fold (IC50 14-15.0 μM). Moreover, the results showed that cancer cell lines are 8- to 12-fold more sensitive to the 3-O-α-l-rhamnopyranoside derivative of betulinic acid (IC50 2.6-3.9 μM, 22) than the healthy cells (IC50 31 μM). Thus, this study indicates that 3-O-glycosides of lupane-type triterpenoids represent an interesting class of potent in vitro cytotoxic agents.

Regio- and Stereoselective Ring Opening of Epoxy Pyranosides with Titanium Isopropoxide Reagents and SmI2: A Straightforward Access to Iododeoxy Sugars

A regioselective synthesis of 3-iodo-3-deoxy sugars is described by trans-diaxial cleavage of the oxirane ring of 2,3-anhydropyranosides with halogenated titanium isopropoxide reagents and samarium iodide.