A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon

Stephens, Benjamin E.; Liu, Fei

doi:10.1016/j.tetlet.2007.10.141

Cited by 7 publications

(1 citation statement)

References 38 publications

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“…The aldehyde 3 was first prepared by a known procedure 14 and subjected to the Grignard reaction with tetradecylmagnesium bromide generated from 1-bromotetradecane and Mg to give the alcohols 4 and 5 in 47% overall yield (Scheme 1). As previously reported, 15 the substrate-induced stereoselectivity favoured the formation of the unwanted isomer 4, and the desired isomer 5 was produced as the minor product with a ratio of 4:5 = 1 Removal of the benzylidene protecting group from 6 was then conducted by treatment with p-TsOH in MeOH-CH 2 Cl 2 to afford 9 16 in 80% yield, which was treated subsequently with NaN 3 under heating to give the azide 10 16 in 74% yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and immunostimulatory activity of two α-S-galactosyl phenyl-capped ceramides

Petrasca¹,

Murphy²,

O’Reilly³

et al. 2013

Arkivoc

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Section: Resultsmentioning

confidence: 99%

Synthesis and immunostimulatory activity of two α-S-galactosyl phenyl-capped ceramides

Petrasca¹,

Murphy²,

O’Reilly³

et al. 2013

Arkivoc

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Ethyl 2-(diphenoxyphosphinyl) acetate

Roy

2013

Encyclopedia of Reagents for Organic Synthesis

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Synthesis of an Oxidation‐Stable Analogue of Cyclic Pyranopterin Monophosphate (cPMP)

et al. 2014

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Molybdenum cofactor (Moco) deficiency is a lethal hereditary metabolic disease. A recently developed therapy requires continuous intravenous supplementation of the biosynthetic Moco precursor cyclic pyranopterin monophosphate (cPMP). The limited stability of the latter natural product, mostly due to oxidative degradation, is problematic for oral administration. Therefore, the synthesis of more stable cPMP analogues is of great interest. In this context and for the first time, the synthesis of a cPMP analogue, in which the oxidation‐labile reduced pterin unit is replaced by a pyrazine moiety, was achieved starting from the chiral pool materials D‐galactose or D‐arabitol. Our synthesis, 13 steps in total, includes the following key transformations: i) pyrazine lithiation, followed by acylation; ii) closure of the pyrane ring by nucleophilic aromatic substitution; and iii) introduction of phosphate.

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A practical and enantiospecific conversion of d-galactose to a substituted α,β-unsaturated δ-lactone synthon

Cited by 7 publications

References 38 publications

Synthesis and immunostimulatory activity of two α-S-galactosyl phenyl-capped ceramides

Synthesis and immunostimulatory activity of two α-S-galactosyl phenyl-capped ceramides

Ethyl 2-(diphenoxyphosphinyl) acetate

Synthesis of an Oxidation‐Stable Analogue of Cyclic Pyranopterin Monophosphate (cPMP)

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