146512-60-9

Upstream product

• 138436-29-0 (R)-2-Benzyloxymethoxymethyl-3-(tert-butyl-diphenyl-silanyloxy)-propionaldehyde 
• 140479-39-6 (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-diphenyl-silanyloxy)-hex-5-en-3-ol 
• 140479-38-5 (2R,3R)-2-Benzyloxymethoxymethyl-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol 

Downstream Products

• 140479-51-2 (4R,5R)-cis-4-allyl-5-(((benzyloxy)methoxy)methyl)-2,2-dimethyl-1,3-dioxane 

Relevant academic research and scientific papers

Synthesis of Both Top and Bottom Fragments of (-)-Talaromycin A through Enantiospecific and Diastereoselective Elaboration of Asymmetrized Tris(hydroxymethyl)methane

Asymmetrized tris(hydroxymethyl)methane equivalents of general formula 5 have been employed as chiral building blocks for the enantiospecific and diastereoselective synthesis of both fragments 3 and 4, whose conversion into Talaromycin A was already reported.Preparation of bottom half fragment 3 was achieved through a "protecting group-controlled" stereoselective allylation of an asymmetrized bis(hydroxymethyl)acetaldehyde with allyltributyltin, while the top half fragment 4 was obtained in high overall yield by sequential elongation of two of the three synthetically equivalent masked hydroxymethyl group of 5, via nucleophilic substitution reactions.

Protecting group controlled diastereoselective allylation of asymmetrized bis (hydroxymethyl) acetaldehydes (BHYMA)

MgBr2 catalysed allylation of a series of diprotected asymmetrized bis (Hydroxymethyl) acetaldehydes 2 with allyltributylstannane proceeds with good diastereoselectivity. The stereochemical results are in line with a cyclic chelated transition state, where only one of the two CH2OR appendages, due to the different nature of protecting groups, is capable of coordinating the Lewis acid.