163395-92-4

Upstream product

• 35028-02-5 1-[4-(benzyloxy)-2,6-dihydroxyphenyl]ethanone 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 

Downstream Products

• 163395-93-5 4-benzyloxy-2,6-bis(4-benzyloxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 
• 169566-46-5 1-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethanone 
• 1064179-44-7 C₆₅H₆₆O₉Si 
• 791601-77-9 7-benzyloxy-5-hydroxy-2-(4-methoxymethoxyphenyl)-6-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-4H-1-benzopyran-4-one 
• 791601-81-5 6-(β-D-glucopyranosyl)-5,7-dihydroxy-2-(4-methoxymethoxyphenyl)-4H-1-benzopyran-4-one 
• 791601-75-7 4-benzyloxy-2-hydroxy-6-(4-methoxymethoxybenzoyloxy)-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)acetophenone 

Relevant academic research and scientific papers

Glucose uptake enhancing activity of puerarin and the role of C-glucoside suggested from activity of related compounds

Chemical treatment of diabetes mellitus is widely studied and controlling of blood glucose level is the main course of therapy. In type 2 diabetes mellitus, insulin resistance is the major problem. An isoflavone C-glucoside, puerarin (1), is known to enhance glucose uptake into the insulin sensitive cell and is thought to be a candidate for treatment of diabetes mellitus. We synthesized 1 and several derivatives to apply for the structure-activity relationship study. The result against 3T3-L1 adipocyte indicated that the C-glucoside part of 1 is unconcerned in its activity when tested in vitro and the main structure responsible for its activity was the isoflavone moiety.

Concise synthesis of chafurosides A and B

The regioselective synthesis of chafurosides A (1) and B (2) from the same methyl ketone 5 was accomplished using a novel protecting group strategy. Both flavone rings were constructed from β-diketone intermediate 4, which was readily obtained by condensation of an acyl donor and ketone 5. Construction of the dihydrofuran ring was achieved via an intramolecular Mitsunobu reaction.

Concise total synthesis of flavone C-glycoside having potent anti-inflammatory activity

The total synthesis of anti-inflammatory active flavone C-glycoside isolated from oolong tea extract is achieved. Introducing a C-glucosyl moiety to an aryl system and constructing a fused tetracyclic ring characteristic to this natural product were condu

Glycosyl Imidates, 69. - Synthesis of Flavone C-Glycosides Vitexin, Isovitexin, and Isoembigenin

2-Hydroxy-4,6-dimethoxyacetophenone (4) was glycosylated with O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate (5) and trimethylsilyl triflate as promoter to yield directly the C-glycoside 6.Construction of the flavone system by application of a Baker-Venkataraman-type rearrangement followed by deprotection yielded isoembigenin (2).Glycosylation of 4,6-bis(tert-butyldimethylsilyloxy)-2-hydroxyacetophenone (17) with the trichloroacetimidate 5 afforded the O-glycoside intermediate 18 which was converted via Fries rearrangement into the C-glycoside 21.Applying again the Baker-Venkataraman rearrangement and cyclization gave isovitexin and vitexin derivatives 25 and 26, which were completely deprotected to yield isovitexin (1b) and vitexin (1a), respectively. - Key Words: Glycosides / Flavones / Vitexin / Isovitexin / Isoembigenin / Carbohydrates / Trichloroacetimidates / Fries rearrangement / Baker-Venkataraman rearrangement