159517-86-9

Upstream product

• 5754-34-7 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 69985-32-6 (R)-4-phenylmethoxy-1,2-butanediol 
• 77-76-9 2,2-dimethoxy-propane 
• 115114-86-8 3,4-O-isopropylidene-L-(S)-erythrulose 

Downstream Products

• 69985-32-6 (R)-4-phenylmethoxy-1,2-butanediol 
• 5754-34-7 2-((4R)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 115114-87-9 (2R)-2-(2-benzyloxyethyl)oxirane 
• 132980-10-0 (R)-4-Benzyloxy-1-chloro-butan-2-ol 
• 132980-14-4 (R)-4-Benzyloxy-2-chloro-butan-1-ol 
• 185155-49-1 (S)-(-)-1-benzyloxy-3-hexadecanol 
• 185155-50-4 (S)-(+)-1-benzyloxy-3-hexadecyl acetate 
• 159424-44-9 (R)-4-O-benzyl-1,2-O-ditosyl-butane-1,2,4-triol 
• 91285-62-0 (S)-1-(benzyloxy)-3-hydroxyhex-5-ene 
• 142592-73-2 (S)-6-(benzyloxy)-1,4-hexanediol 

Relevant academic research and scientific papers

Carbohydrate-Catalyzed Enantioselective Alkene Diboration: Enhanced Reactivity of 1,2-Bonded Diboron Complexes

Catalytic enantioselective diboration of alkenes is accomplished with readily available carbohydrate-derived catalysts. Mechanistic experiments suggest the intermediacy of 1,2-bonded diboronates.

Intramolecular thermal stepwise [2 + 2] cycloadditions: Investigation of a stereoselective synthesis of [n.2.0]-bicyclolactones

Fused cyclobutanes are found in a range of natural products and formation of these motifs in a straightforward and easy manner represents an interesting synthetic challenge. To this end we investigated an intramolecular variant of the thermal enamine [2 + 2] cyclisation, developing a diastereoselective intramolecular enamine [2 + 2] cyclisation furnishing δ lactone and lactam fused cyclobutenes in good yield and excellent diastereoselectivity.

Rational synthesis of contra-thermodynamic spiroacetals by reductive cyclizations

A synthesis of spiroacetals was developed using a reductive cyclization strategy that leads stereoselectively to spiroacetals with a single anomeric stabilization. The method begins with the synthesis of spiro ortho esters. The ortho ester is converted to a cyano acetal. Reductive lithiation of the cyano acetal generates an axial dialkoxylithium reagent, and intramolecular cyclization produces a new ring with retention of configuration. The strategy is convergent and produces complex spiro acetals in only a few steps. The method will be useful in the synthesis of natural products and will facilitate the synthesis of previously inaccessible contra-thermodynamic acetals. Copyright

Synthesis of (S)- and (R)-3-hydroxyhexadecanoic acid

Diol (R)-(+)-3 is prepared either from the hydroxyketone 2 by reduction with fermenting baker's yeast or by hydrolysis of the dioxolane (R)-(+)-1 which is available from dimethyl D-malate as starting material. (R)-(+)-3 could be converted stereoselectively into (R)-(+)-4. Reaction of (+)-4 with dodecylmagnesium bromide yielded the alcohol (S)-(-)-5 with >99% ee. Its acetylation gave (S)-(+)-6 and hydrogenolysis gave the primary alcohol (S)-(+)-7 which could be oxidized selectively to (S)-(+)-8 wih NaIO4/RuCl3. Alkaline hydrolysis of (+)-8 yielded 3-hydroxyhexadecanoic acid (S)-(+)-9 which could be esterified to give the methyl ester (S)-(+)-10 with >99% ee. Starting with the dioxolane (S)-(-)-1, derived from dimethyl L-malate, the 3-hydroxyhexadecanoic acid (R)-(-)-10 could be synthesised via the intemediates (S)-(-)-3, (S)-(-)-4, (R)-(+)-5, (R)-(-)-6, (R)-(-)-7 and (R)-(-)-8. Copyright (C) Elsevier Science Ltd.

A Difference CD Method for Determining Absolute Stereochemistry of Acyclic 1,2,4-Triols

A general method based on difference circular dichroic (DIF CD) spectroscopy for assigning the absolute configuration of 1,2,4-triol is presented.Four possible stereoisomers of 6-heptene-1,2,4-triol were prepared and served as models to develop the procedure.The sign of the DIF CD Cotton effect is correlated to the absolute configuration of the C2 position.

Synthesis and catalytic properties of an acyclic analogue of hydroxy norphos

The synthesis of (S)-1,2-bis(diphenylphosphino)butane-4-ol 1 an acyclic analogue of hydroxy norphos is described, starting from L-ascorbic acid. Problems which arose during the cleavage of OH-protective groups in the presence of phosphino groups are discu

L-(S)-ERYTHRULOSE : THE SYNTHESYS OF (R)-1,2,4-BUTANETRIOL AND OF SOME RELATED C4 CHIRONS.

L-(S)-Erythrulose can easily be transformed into (R)-1,2,4-butanetriol and related C4 chiral building blocks.A formal synthesis of (-)-GABOB is presented.Also the formation of 3-methylene-1,2,4-butanetriol derivatives is described.