1240795-78-1

Basic information

• Product Name: (2R,3S,4S,4aR,10bS)-8,10-bis(benzyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
• Synonyms: (2R,3S,4S,4aR,10bS)-8,10-bis(benzyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one
• CAS NO: 1240795-78-1
• Molecular Weight: 508.525
• Mol File: 1240795-78-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,4aR,10bS)-8,10-bis(benzyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,4aR,10bS)-8,10-bis(benzyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one(1240795-78-1)
• EPA Substance Registry System: (2R,3S,4S,4aR,10bS)-8,10-bis(benzyloxy)-3,4-dihydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one(1240795-78-1)

Safety Data

• Hazardous Substances Data: 1240795-78-1(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 477-90-7 bergenin 
• 262266-33-1 1,5-anhydro-2-deoxy-4,6-O-bis(tert-butylsilylidene)-3-O-triisopropylsilyl-D-arabino-hex-1-enitol 
• 191593-14-3 4,6-O-di(tert-butyl)silanediyl-D-glucal 
• 13326-69-7 methyl 3,5-bis(benzyloxy)-4-methoxybenzoate 
• 100-39-0 benzyl bromide 
• 24093-81-0 methyl 3,5-dihydroxy-4-methoxybenzoate 
• 13089-97-9 methyl 3,5-diacetoxy-4-methoxy benzoate 
• 20189-90-6 3,4,5-triacetoxy-benzoic acid methyl ester 
• 99-24-1 methyl galloate 
• 842132-50-7 1,5-anhydro-2-deoxy-4,6-O-di-(tert-butyl)silanediyl-3-O-triisopropylsilyl-D-arabino-hex-1-enitolylboronic acid pinacol ester 
• 13265-84-4 D-glucal 

Downstream Products

• 1329446-52-7 C₂₁H₂₀O₁₂ 

Relevant articles and documents

Synthesis and biological evaluation of bergenin derivatives as new immunosuppressants

Bergenin, which is isolated from Bergenia species, exhibits various pharmacological properties. In the search for new types of immunosuppressants, a series of bergenin derivatives were designed and synthesized, and their immunosuppressive effects were eva

Synthesis and in?vitro and in?vivo antitumour activity study of 11-hydroxyl esterified bergenin/cinnamic acid hybrids

Fourteen bergenin/cinnamic acid hybrids were synthesized, characterized and evaluated for their antitumour activity both in?vitro and in?vivo. The most potent compound, 5c, arrested HepG2 cells (IC50?=?4.23?±?0.79?μM) in the G2/M phase and induced cellular apoptosis. Moreover, compound 5c was also found to suppress the tumour growth in Heps xenograft-bearing mice with low toxicity. In the mechanistic study, 5c administration ignited a mitochondria-mediated apoptosis pathway of HepG2 cell death. Furthermore, 5c activated Akt-dependent pathways and further decreased the expression of the Bcl-2 family of proteins. The downstream mitochondrial p53 translocation was also significantly activated, accompanied by an increase of the caspase-9, caspase-3 activation. These data imply that bergenin/cinnamic acid hybrids could serve as novel Akt/Bcl-2 inhibitors for further preclinical studies.

Cross-coupling reaction of saccharide-based alkenyl boronic acids with aryl halides: The synthesis of bergenin

A convenient synthetic pathway enabling D-glucal and D-galactal pinacol boronates to be prepared in good isolated yields was achieved. Both pinacol boronates were tested in a series of cross-coupling reactions under Suzuki-Miyaura cross-coupling conditions to obtain the corresponding aryl, heteroaryl, and alkenyl derivatives in high isolated yields. This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the first total synthesis of bergenin. Building blocks with boron: A convenient synthetic route to D-glucal and D-galactal pinacol boronates was developed, and the boronates were used in cross-coupling reactions to generate the corresponding aryl, heteroaryl, and alkenyl derivatives in high yields (see scheme). This methodology was applied to the formal synthesis of the glucopyranoside moiety of papulacandin D and the total synthesis of bergenin.