172919-15-2

Upstream product

• 4049-39-2 4-benzyloxy-3-hydroxy-benzaldehyde 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 1390643-78-3 (2R,3S)-3'-O-(tert-butyldimethylsilyl)-5,7,4'-tri-O-benzylcatechin 
• 1390643-81-8 (2R)-3'-(tert-butyldimethylsilyloxy)-5,7,4'-tribenzyloxyflavan-3-one 
• 1390643-84-1 (2R,3R)-3'-O-(tert-butyldimethylsilyl)-5,7,4'-tri-O-benzyl-epi-catechin 
• 1390643-69-2 C₃₆H₃₄O₇ 
• 1390643-87-4 (2R,3R)-3'-(tert-butyldimethylsilyl)-5,7,4'-tri-O-benzyl-3-acetylepicatechin 
• 1390643-89-6 (2R,3R)-5,7,4'-tri-O-benzyl-3-acetylepicatechin 
• 1390643-91-0 C₅₁H₅₀O₁₆ 
• 1390644-13-9 C₅₁H₅₀O₁₆ 
• 1390643-95-4 (2R,3R)-5,7,4'-tri-O-benzylepicatechin 
• 1390643-97-6 (2R,3R)-5,7,4'-tri-O-benzylepicatechin-3'-O-neopentylsulfonate 
• 1390643-99-8 sodium (2R,3R)-5,7,4'-tri-O-benzylepicatechin-3'-O-sulfonate 
• 1422182-77-1 sodium (2R,3R)-epicatechin-3'-O-sulfonate 
• 1390643-72-7 (2R,3S)-5,7,4'-tri-O-benzyl-3-O-acetylcatechin 
• 1390644-01-5 (E)-2-(benzyloxy)-5-(3-hydroxyprop-1-en-1-yl)phenol 

Relevant academic research and scientific papers

Epicatechin B-ring conjugates: First enantioselective synthesis and evidence for their occurrence in human biological fluids

Herein, the first enantioselective total synthesis of a number of biologically relevant (-)-epicatechin conjugates is described. The success of this synthesis relied on (i) optimized conditions for the stereospecific cyclization step leading to the catechin C ring; on (ii) efficient conjugation reactions; and on (iii) optimized deprotection sequences. These standard compounds have been subsequently used to elucidate for the first time the pattern of (-)-epicatechin conjugates present in four different human biological fluids following (-)-epicatechin absorption.

Antineoplastic agents. 565. Synthesis of combretastatin D-2 phosphate and dihydro-combretastatin D-2

A modified synthetic route to combretastatin D-2 (5) was devised in order to further evaluate its biological activity, for its conversion to phosphate prodrugs (25-28), and as a route to obtaining dihydro-combretastatin D-2 (42). A parallel first total synthesis of dihydro-combretastatin D-2 was completed, proceeding from a saturated 3-phenylpropionic ester intermediate via the Ullmann biaryl ether reaction (39-41). In contrast to the cancer cell growth inhibitory activity exhibited by combretastatin D-2, relatively minor structural modifications (41, 42) caused elimination of those properties.

Total synthesis of combretastatins D

The 15-membered caffrane ring of the natural product group of combretastatins D is synthesized in high yield with suitably functionalized saturated seco acids. The key step is a Mitsunobu-type macrolactonization. A common synthon is used for the construct