947619-70-7

Upstream product

• 603040-45-5 C₁₃H₁₆O₃ 
• 103625-11-2 (2S)-pent-4-ene-1,2-diol 
• 824-94-2 p-methoxybenzyl chloride 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 911237-03-1 (R)-4-Isopropyl-3-[(S)-2-(4-methoxy-benzyloxy)-pent-4-enoyl]-oxazolidin-2-one 
• 911237-04-2 (2S)-2-(4-methoxybenzyloxy)-4-pentenol 

Downstream Products

• 1433460-01-5 (4S,7R,Z)-7-[(tert-butyldiphenylsilyloxy)methyl]-4-(4-methoxybenzyloxy)non-5-en-2-one 
• 1433460-00-4 C₃₃H₄₂O₄Si 
• 1433460-07-1 (3S,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one 
• 1433460-08-2 (3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one 
• 1433459-96-1 tert-butyl [(2R,5S,Z)-2-ethyl-5-(4-methoxybenzyloxy)octa-3,7-dienyloxy]diphenylsilane 
• 1433459-97-2 tert-butyl [(2S,5S,Z)-2-ethyl-5-(4-methoxybenzyloxy)octa-3,7-dienyloxy]diphenylsilane 
• 108794-64-5 (S)-methyl 2-hydroxyvalerate 

Relevant academic research and scientific papers

E-Selectin Antagonists Modified By Macrocycle Formation to the Galactose

Provided herein are glycomimetic E-selectin antagonist compounds of formula (I)) and pharmaceutical compositions comprising at least one of the same. The compounds of the present disclosure include trisaccharide domain mimics comprising at least one macro

E-SELECTIN ANTAGONISTS MODIFIED BY MACROCYCLE FORMATION TO THE GALACTOSE

Provided herein are glycomimetic E-selectin antagonist compounds of formula (I)) and pharmaceutical compositions comprising at least one of the same. The compounds of the present disclosure include trisaccharide domain mimics comprising at least one macro

Convergent strategy towards the synthesis of restricted analogues of peloruside A

A rapid convergent strategy to access unsaturated analogues of peloruside A has been demonstrated. This is depicted as an original C11-C12 aldol connection between a C12-C20 ketone fragment and a C2-C11 pyran fragment bearing an aldehyde function, with high yield and a good level of diastereoselectivity. The desired unsaturated macrocycle was obtained by a late-stage ring closing metathesis reaction.

Enantioselective total synthesis of brevetoxin A: Unified strategy for the B, E, G, and J subunits

Brevetoxin A is a decacyclic ladder toxin that possesses 5-, 6-, 7-, 8-, and 9-membered oxacycles, as well as 22 tetrahedral stereocenters. Herein, we describe a unified approach to the B, E, G, and J rings based upon a ring-closing metathesis strategy from the corresponding dienes. The enolate technologies developed in our laboratory allowed access to the precursor acyclic dienes for the B, E, and G medium-ring ethers. The strategies developed for the syntheses of these four monocycles ultimately provided multigram quantities of each of the rings, supporting our efforts toward the completion of a convergent synthesis of brevetoxin A.

Improved synthesis of the ABCDE fragment of brevetoxin A

A second-generation synthesis of the BCDE fragment of brevetoxin A is described. Novel reactions were developed that extend the utility of the asymmetric glycolate alkylation reaction and improve scale-up to provide gram quantities of the B and E subunits