562823-58-9

Upstream product

• 562823-56-7 {(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 
• 562823-70-5 (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester 
• 562823-69-2 (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester 
• 162473-68-9 methyl 5-(tert-butyldiphenylsilyl)oxy-2-pentenoate 
• 127665-77-4 (E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol 
• 562823-71-6 2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 59779-75-8 diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 
• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 256494-25-4 (E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate 
• 100-39-0 benzyl bromide 

Downstream Products

• 562823-72-7 1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol 
• 1054661-39-0 1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-one 
• 562823-59-0 (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol 
• 562823-61-4 (S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one 
• 562823-60-3 Acrylic acid (S)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-but-3-enyl ester 
• 562823-65-8 (Z)-(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester 
• 562823-66-9 (2S,3S,5S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-hexanoic acid methyl ester 

Relevant academic research and scientific papers

A facile approach for the synthesis of C13-C24 fragments of maltepolides A, C and D

A linear, chiron approach for the synthesis of C13-C24 fragments of cytostatic maltepolides A, C and D consisting of a tetrahydrofuran subunit and a chiral alkenyl/alkyl substituent is achieved from (+)-diethyl l-tartrate. The other chiral stereocenters were generated by employing key reactions such as Crimmins aldol, alkynylation and CeCl3·7H2O mediated Luche reduction reactions.

Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl-4-butanolides in Relation to PGE2

Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [3H]-PGE2 binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE 2. Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A

A stereocontrolled synthesis of the C1-C9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral β-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an α,β-unsaturated δ-lactone.