210890-98-5

Upstream product

• 331-39-5 caffeic acid 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 203118-31-4 di-O-t-butyldimethylsilylcaffeic acid t-butyldimethylsilyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 203118-32-5 (E)-3-(3,4-bis((tert-butyldimethylsilyl)oxy)phenyl)acrylic acid 

Downstream Products

• 106972-94-5 calceolarioside B 
• 302576-68-7 2-(4-((phenoxythioxomethyl)amino)phenyl)ethyl O,O-(3,4-bis(1,1,2,2-tetramethyl-1-silapropyl))caffeic acid ester 
• 203118-33-6 (E)-3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-acrylic acid (S)-1-allyloxycarbonyl-2-(3,4-bis-allyloxy-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Synthesis of glucosamine derivative with double caffeic acid moieties at N– and 6-O-positions for developments of natural based materials

Glucosamine derivatives with double caffeic acid moieties were synthesized for developments of natural based materials. Caffeic acids were introduced to glucosamine derivatives through the synthesis roots as protection and de-protection reactions. Firstly, the silyl groups and tert-butoxycarbonyl groups were selected for the protection of each hydroxyl group and amino group. The designed glucosamine derivative showed reactivity of the double bonds, which was confirmed by UV spectra. Photoresponsivity was observed both in solution and heterogeneous suspension. The oligomerization was also confirmed in water suspension. The solubility and thermal stability were changed after the UV irradiation. This results show the potential of great progress a natural based material development.

Chitosan-hydroxycinnamic acid conjugates: Optimization of the synthesis and investigation of the structure activity relationship

A new synthesis method was developed and optimized by a full factorial design for conjugating hydroxycinnamic acids (HCA-s) to chitosan. Cinnamic acid and tert-butyldimethylsilyl protected HCA-s were converted to their corresponding acyl chlorides and rea

Glucosamine derivative

To provide a novel substance useful as a functional substance having a biomass-derived structure and a composite function.SOLUTION: A glucosamine derivative is represented by formula (I) (Ris H, a protective group of a hydroxy group or an organic group other than the hydroxy group protective group; R-Rare different from Rand independently represent H or a hydroxy group protective group; n is an integer of 2-5; and Rindependently represent H or a phenolic hydroxyl group protective group).SELECTED DRAWING: None

The total synthesis of sevanol, a novel lignan isolated from the thyme plant (Thymus armeniacus)

Recently, a novel lignan sevanol was isolated from the thyme plant Thymus armeniacus. During structure-functional elucidation it showed significant biological activity on ASIC3 acid sensing channels. Herein we describe the first synthesis of sevanol with

Short synthesis of phenylpropanoid glycosides calceolarioside-B and eutigoside-A

A convenient 4-step synthesis of calceolarioside-B 1 and eutigoside-A 2 in high overall yield is described. The key step involved the regioselective, Me2SnCl2-catalyzed O-6 acylation of unprotected 2-phenylethyl-β-D-glucosides 5a–b with cinnamoyl chlorides 6a–b in excellent yields. Acylation at O-6 is selective with the acid chlorides used. This work serves as a model for the convenient synthesis of phenylpropanoid glycosides acylated at O-6.

USE OF ROSMARINIC ACID AND DERIVATIVES THEREOF AS AN IMMUNOSUPPRESSANT OR AN INHIBITOR OF SH2-MEDIATED PROCESS

The present invention relates to use of rosmarinic acid and/or derivatives thereof as immunosuppressive agents and/or as inhibitor of SH2 domain function. Disclosed in the present invention is that rosmarinic acid and derivatives thereof specifically inhibit the binding of ligand peptides to Lck SH2 domain, disturb the Lck-mediated signal transduction in T cells, also inhibit cytoline gene expression, and suppress immune responses in the transplanted tissue. These activities of rosmarinic acid and derivatives thereof support their applicability to treatment, prevention and/or diagnosis of graft rejection, GVHD, autoimmune diseases, inflammatory diseases, etc.

Styrylquinoline derivatives: A new class of potent HIV-1 integrase inhibitors that block HIV-1 replication in CEM cells

On the basis of the fact that several polynucleotidyl transferases, related to HIV integrase, contain in their active site two divalent metal cations, separated by ca. 4 ?, new potential HIV integrase inhibitors were designed, in which a quinoline substructure is linked to an aryl nucleus possessing various hydroxy substitution patterns, by means of an ethylenic spacer. Although the most active compounds contain the catechol structure, this group is not essential for the activity, since compound 21 that lacks such a moiety is a potent drug, implicating the presence of a different pharmacophore. The most promising styrylquinolines thus synthesized inhibit HIV-1 integrase in vitro at micromolar or submicromolar concentrations and block HIV replication in CEM cells, with no significant cellular toxicity in a 5-day period assay. These inhibitors are active against integrase core domain-mediated disintegration, suggesting that fragment 50-212 is their actual target. These new styrylquinolines may provide lead compounds for the development of novel antiretroviral agents for AIDS therapeutics, based upon inhibition of HIV integrase. They might also be used in the elucidation of the mechanism of inhibition of this enzyme; e.g., they could serve as candidates for cocrystallization studies with HIV integrase.

A non-enzymatic synthesis of (S)-(-)-rosmarinic acid and a study of a biomimetic route to (+)-rabdosiin

The synthesis of (S)-(-)-rosmarinic acid (30) in 9% overall yield is described. The synthesis was achieved by a convergent route in which 3-(3′,4′-dihydroxyphenyl)-(S)-lactic acid (23) and caffeic acid (25), both appropriately protected, were coupled to produce a pentaallyl precursor 29, which was then deprotected to give (S)-(-)-rosmarinic acid (30). A triallyl derivative 35 was similarly prepared and converted to (+)-rabdosiin (41) and its (1R,2S) isomer (42) via a biomimetic oxidative free radical coupling-cyclization followed by deallylation. The coupling-cyclization gave a ratio of rabdosiin diastereomers unlike that found in nature. A preliminary study showed that methyl (R)-mandelyl sinapate (15) could be dimerized diastereoselectively to give a 1,2-trans thomasidioate diester (16). The synthesis of (S)-(-)-rosmarinic aid (30) in 9% overall yield is described. The synthesis was achieved by a convergent route in which 3- (3',4'-dihydroxyphenyl)-(S)-lactic acid (23) and caffeic acid (25), both appropriately protected, were coupled to produce a pentaallyl precursor 29, which was then deprotected to give (S)-(-)-rosmarinic acid (30). A triallyl derivative 35 was similarly prepared and converted to (+)-rabdosiin (41) and its (1R,2S) isomer (42) via a biomimetic oxidative free radical coupling- cyclization followed by deallylation. The coupling-cyclization gave a ratio of rabdosiin diastereomers unlike that found in nature. A preliminary study showed that methyl (R)-mandelyl sinapate (15) could be dimerized diastereoselectively to give a 1,2-trans thomasidioate diester (16).