120969-06-4

Basic information

• Product Name: diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside
• Synonyms: diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside
• CAS NO: 120969-06-4
• Molecular Weight: 993.204
• Mol File: 120969-06-4.mol

Chemical Properties

• CAS DataBase Reference: diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside(120969-06-4)
• EPA Substance Registry System: diosgenyl 2,3,4,6-O-tetra-benzoyl-β-D-glucuronopyranoside(120969-06-4)

Safety Data

• Hazardous Substances Data: 120969-06-4(Hazardous Substances Data)

Upstream product

• 105376-04-3 ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-glucopyranoside 
• 512-04-9 diosgenin 
• 339276-12-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 
• 1221151-98-9 2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl ortho-(hex-1-ynyl)benzoate 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 151767-11-2 2,3,4,5-tetra-O-benzoyl-D-glucopyranosyl trichloroacetimidate 
• 627466-64-2 2,3,4,6-tetra-O-benzoyl-D-glucopyranose 
• 165877-99-6 2,3,4,6-tetra-O-Bz-β-D-glucopyranosyl bromide 
• 149707-76-6 O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl) trichloroacetimidate 

Downstream Products

• 14144-06-0 trillin 
• 60478-68-4 dioscin 
• 211797-89-6 diosgenyl 4,6-O-benzylidene-β-D-glucopyranoside 
• 484002-05-3 C₄₄H₆₀O₁₀ 
• 484002-06-4 diosgenin-3-yl 2,3-di-O-acetyl-6-O-(2,3,4-tri-O-benzoyl-L-arabpyranosyl)-D-glucopyranoside 

Relevant articles and documents

Synthesis and antitumor activity of icogenin and its analogue

Natural saponin icogenin, namely 25(S)-22-O-methyl-furost-5-en-3β,26- dio-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-glucopyranosyl-(1 → 3)]-β-d-glucopyranoside, and one of its analogues, 25(S)-22-O-methyl-furost-5-en-3β,26-dio-3-O-α-l-rhamnopyranosyl-(1 → 2)-[

Facile sythesis of dioscin and its analogues

Three representative spirostanol saponins that have typical structure of the sugar moiety, diosgenyl 2,3-di-O-α-L-rhamnopyranosyl-β-D- glucopyranoside, diosgenyl 2,4-di-O-α-L-rhamnopyranosyl-β-D- glucopyranoside (dioscin), and diosgenyl 2,6-di-O-α-L-rhamnopyranosyl- β-D-glucopyranoside, were synthesized in a facile way. An approach to selectively mask the C3-hydroxyl of diosgenyl 4,6-O-benzylidene β-D-glucopyranoside was described. A procedure using cerium(IV) ammonium nitrate for selective removal of tert-butyldimethylsilyl group while retaining levulinyl group is afforded. Copyright

N-Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies

We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature. The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentiotetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.

STEROID SAPONINS WITH ANTI-CANCER ACTIVITY

The present invention relates to a new class of steroid saponins that have interesting biological activity. In particular the present invention relates to a class of steroid saponins in which the sugar moiety has been selectively functionalised to introdu

Solasodine-3-O-β-D-glucopyranoside kills Candida albicans by disrupting the intracellular vacuole

The increasing incidence of fungal infections and emergence of drug resistance underlie the constant search for new antifungal agents and exploration of their modes of action. The present study aimed to investigate the antifungal mechanisms of solasodine-3-O-β-D-glucopyranoside (SG) isolated from the medicinal plant Solanum nigrum L. In vitro, SG displayed potent fungicidal activity against both azole-sensitive and azole-resistant Candida albicans strains in Spider medium with its MICs of 32 μg/ml. Analysis of structure and bioactivity revealed that both the glucosyl residue and NH group were required for SG activity. Quantum dot (QD) assays demonstrated that the glucosyl moiety was critical for SG uptake into Candida cells, as further confirmed by glucose rescue experiments. Measurement of the fluorescence intensity of 2′,7'-dichlorofluorescin diacetate (DCFHDA) by flow cytometry indicated that SG even at 64 μg/ml just caused a moderate increase of reactive oxygen species (ROS) generation by 58% in C. albicans cells. Observation of vacuole staining by confocal microscopy demonstrated that SG alkalized the intracellular vacuole of C. albicans and caused hyper-permeability of the vacuole membrane, resulting in cell death. These results support the potential application of SG in fighting fungal infections and reveal a novel fungicidal mechanism.

IMPROVED SYNTHESIS

The present invention provides an improved synthesis of a class of steroid saponins. Furthermore, the present invention provides a method of selectively discriminating between the C2 and C3 hydroxyl groups of a mono-glycosylated steroid saponin – a key step in the preparation of this class of compounds. Additionally, the present invention provides a range of steroid saponin derivatives, and methods of making them.

Glycosyl N-tosyl benzimidate as a new building block for chemical glycosylation

Seven novel glycosyl N-tosyl benzimidates were prepared by the reactions of the corresponding hemiacetals with imidoyl chloride in 55-88% yields, which were smoothly converted to glycosides, upon treatment with alcohols and catalytic TMSOTf, in 57-99% yields. Georg Thieme Verlag Stuttgart · New York.

An improved synthesis of methyl protodioscin. II. A direct E-ring opening by BF3-Et2O/Ac2O from dioscin ester

A direct E-ring opening of dioscin ester by BF3-Et 2O/Ac2O was studied, and methyl protodioscin was synthesized from dioscin ester in three steps with a total yield of 44%. The details of the E-ring opening reaction was di

An efficient glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors under the catalysis of Ph3PAuOTf

A new and powerful glycosylation protocol with glycosyl ortho-alkynylbenzoates as donors and Ph3PAuOTf as a promoter is disclosed. The donors are readily available and stable; the glycosidic coupling yields are generally excellent; the promotion system is catalytic, neutral, and orthogonal to the known glycosylation conditions.

Synthesis of novel spirostanic saponins and their cytotoxic activity

This study was carried out to assess the cytotoxicity of several new synthetic steroidal saponins against the human myeloid leukemia cell lines (HL-60 and U937) and against human melanoma cells (SK-MEL-1). Several diosgenyl glycosides analyzed showed strong cell growth inhibition which was associated with alterations in cell cycle progression and induction of apoptosis. Studies of cytochrome c release and caspase-9 activation suggest a main role of the intrinsic pathway of apoptosis in the mechanism of cytotoxicity caused by this kind of compounds.