101833-22-1

Basic information

• Product Name: ETHYL4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE
• Synonyms: ETHYL4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE;Ethyl4,6-O-benzylidene-b-D-galactopyranoside
• CAS NO: 101833-22-1
• Molecular Formula: C₁₅H₂₀O₆
• Molecular Weight: 296.32
• Mol File: 101833-22-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE(101833-22-1)
• EPA Substance Registry System: ETHYL4,6-O-BENZYLIDENE-BETA-D-GALACTOPYRANOSIDE(101833-22-1)

Safety Data

• Hazardous Substances Data: 101833-22-1(Hazardous Substances Data)

Upstream product

• 18997-88-1 1-O-ethyl-β-D-galactopyranoside 
• 60-29-7 diethyl ether 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 3198-49-0 ethyl D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 100-52-7 benzaldehyde 
• 97-30-3 methyl-alpha-D-glucopyranoside 

Relevant articles and documents

Synthesis of alkyl α- and β-d-glucopyranoside-based chiral crown ethers and their application as enantioselective phase-transfer catalysts

Chiral monoaza-15-crown-5-type lariat ethers annelated to alkyl 4,6-O-benzylidene-α- and β-d-glucopyranosides have been synthesized. These macrocycles generated significant asymmetric induction as phase-transfer catalysts in a few two-phase reactions. The catalytic effect of the lariat ethers with methoxy, ethoxy, and i-propoxy substituents on C-1 of the sugar unit in both α and β positions was compared. In liquid–liquid two-phase reactions, the nature and position of the substituents did not have much effect. The α-anomers were somewhat more efficient in terms of enantioselectivity than the β forms. In asymmetric Darzens condensations, in the epoxidation of trans-chalcone, in the Michael addition of β-nitrostyrene and diethyl acetamidomalonate, and in the reaction of 2-benzylidene-1,3-indandione with diethyl bromomalonate, maximum enantioselectivities of 73, 94, 78, and 72%, respectively, were obtained in presence of glucopyranoside-based lariat ethers as catalysts.

The synthesis and antitumor activity of twelve galloyl glucosides

Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-?±-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-?±-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-?2-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-?2-D-glucopyranose (1), 1,4,6-tri-O-galloyl-?2-D-glucopyranose (2), 1,2-di-O-galloyl-?2-D-glucopyranose (3), 1,3-di-O-galloyl-?2-D-glucopyranose (4), 1,2,3-tri- O-galloyl-?±-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-?±-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 ??g/mL, and their IC50 values were determined to be varied in 17.2-124.7 ??M on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 ??g/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.

Sialyl Lex analogues as inhibitors of cellular adhesion

The inventive compounds are analogues of sialyl Lex that inhibit cellular adhesion between a selectin and cells that express sialyl Lex on their surfaces, and their synthetic intermediates. An inventive compound has structure A, STR1