444809-35-2

Upstream product

• 128461-65-4 3-(p-methoxybenzyloxy)propanal 
• 74-86-2 acetylene 
• 4301-14-8 acetylenemagnesium bromide 
• 2746-25-0 p-Methoxybenzyl bromide 
• 54655-07-1 lithium trimethylsilylacetylenide 
• 135362-69-5 3-(4-methoxybenzyl)oxypropan-1-ol 
• 5689-71-4 2-(4-methoxy-phenyl)-[1,3]dioxane 

Downstream Products

• 1276692-84-2 4a,8a-bis(4-methoxyphenethyl)octahydrodifuro[2,3-b:2',3'-e][1,4]dioxine 
• 152329-55-0 (E)-(3R,6S)-4,5-Dibromo-1,8-bis-(4-methoxy-benzyloxy)-oct-4-ene-3,6-diol 

Relevant academic research and scientific papers

Bioorthogonal Hydroamination of Push–Pull-Activated Linear Alkynes

A bioorthogonal reaction between N,N-dialkylhydroxylamines and push–pull-activated halogenated alkynes is described. We explore the use of rehybridization effects in activating alkynes, and we show that electronic effects, when competing stereoelectronic and inductive factors are properly balanced, sufficiently activate a linear alkyne in the uncatalyzed conjugative retro-Cope elimination reaction while adequately protecting it against cellular nucleophiles. This design preserves the low steric profile of an alkyne and pairs it with a comparably unobtrusive hydroxylamine. The kinetics are on par with those of the fastest strain-promoted azide-alkyne cycloaddition reactions, the products regioselectively formed, the components sufficiently stable and easily installed, and the reaction suitable for cellular labeling.

Distinct chemoselectivities in the platinum-catalyzed 1,2- carboalkoxylations of 5-alkoxypent-1-yn-3-ol derivatives

Two distinct Pt-catalyzed carboalkoxylations of alkynes are reported. The cycloisomerization of 5-alkoxypent-1-yn-3-ol derivatives 5 produces 2,6-dioxabicyclo[3.1.0]hexanes 6; the mechanism is postulated to involve a hydroxyl-triggered [3.3]-sigmatropic a

A study toward a total synthesis of fostriecin

In order to synthesize the major C(3)-C(12) part of fostriecin, asymmetric dihydroxylation of several dienes 5a-f, prepared by cross-coupling reactions of several types, was studied, thus providing high dependency on the hydroxyl groups at C(5) and C(11). The best regioselectivity was obtained with 5d to produce diol 23, which was later transformed into the advanced intermediate 26.

Desymmetrisation of meso propargylic diols

Meso acetylenic diols, conveniently separated from their threo isomers via the corresponding adducts with bromine, have been converted into optically pure derivatives by either lipase-catalysed hydrolysis of the corresponding diacetates or ketalisation of (+)-menthone.