153255-54-0

Upstream product

• 147849-60-3 Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate 
• 147849-58-9 tert-Butyl (R)-4-benzyloxy-3-hydroxybutanoate 
• 147849-59-0 tert-Butyl (S)-4-benzyloxy-3-hydroxybutanoate 
• 95967-46-7 tert-Butyl 4-benzyloxy-3-oxobutanoate 
• 114784-19-9 (R)-Methyl 4-benzyloxy-3-hydroxybutanoate 
• 32122-09-1 ethyl benzyloxyacetate 
• 153324-80-2 (R)-1-Benzyloxy-3-((2R,3S)-3-phenylsulfanylmethyl-oxiranyl)-propan-2-ol 
• 153324-79-9 (R)-1-Benzyloxy-3-((2R,3R)-3-hydroxymethyl-oxiranyl)-propan-2-ol 
• 153255-48-2 (R)-6-Benzyloxy-hex-2-yne-1,5-diol 
• 153255-49-3 (E)-(R)-6-Benzyloxy-hex-2-ene-1,5-diol 
• 14618-80-5 (R)-benzyl glycidol 
• 147849-63-6 tert-butyl (5R)-3-oxo-5-hydroxy-6-benzyloxyhexanoate 
• 147849-64-7 tert-butyl (S)-6-(benzyloxy)-5-hydroxy-3-oxohexanoate 

Downstream Products

• 296785-16-5 (4R,6R)-6-(benzyloxymethyl)-4-methoxy-tetrahydro-2H-pyran-2-one 
• 310883-86-4 (4R,6R)-6-hydroxymethyl-4-methoxy-tetrahydro-2H-pyran-2-one 
• 296785-20-1 (2S,4R,6R)-2-[4-((E)-2-[(2R,3S,4S,5S,6R)-3,5-dimethyl-6-(2-trimethylsilyloxyethyl)-4-triphenylsilyloxy-tetrahydro-2H-pyran-2-yl]prop-1-enyl)(1,3-oxazol-2-yl)]methyl-4-methoxy-6-triethylsilyloxymethyl-tetrahydro-2H-pyran-2-ol 

Relevant academic research and scientific papers

Application of complex aldol reactions to the total synthesis of phorboxazole B

The synthesis of phorboxazole B has been accomplished in 27 linear steps and an overall yield of 12.6%. The absolute stereochemistry of the C4-C12, C33-C38, and C13-C19 fragments was established utilizing catalytic asymmetric aldol methodology, while the absolute stereochemistry of the C20-C32 fragment was derived from an auxiliary-based asymmetric aldol reaction. All remaining chirality was incorporated through internal asymmetric induction, with the exception of the C43 stereocenter which was derived from (R)-trityl glycidol. Key fragment couplings include a stereoselective double stereodifferentiating aldol reaction, a metalated oxazole alkylation, an oxazole-stabilized Wittig olefination, and a chelation-controlled addition of the fully elaborated alkenyl metal side chain.

Asymmetric Hydrogenation of 3,5-Dioxoesters Catalyzed by Ru-binap Complex: A Short Step Asymmetric Synthesis of 6-Substituted 5,6-dihydro-2-pyrones

Asymmetric hydrogenation of 3,5-dioxoesters 1a-c using Ru2Cl4((R) or (S)-binap)2(NEt3) as the catalyst gave dominantly anti 3,5-dihydroxyesters 2, which were then converted into unsaturated lactones 5a-b (ca. 80percent e.e.).The pathway of the hydrogenation reaction was also investigated by asymmetric hydrogenation of (R)- or (S)-5-hydroxy-3-oxoesters 8a-c.It was revealed that the Ru-binap catalyzed hydrogenation of 1a-b proceed dominantly via the β-diketone mode.A convenient asymmetric synthesis of hydroxylactone 3c and unsaturated lactone 5c was presented.Key words: 3,5-dioxoester; Ru-binap catalyst; asymmetric hydrogenation; asymmetric synthesis; lactone

Diastereodivergent synthesis of optically active trans- and cis-6-benzyloxymethyl-4-hydroxytetrahydro-2-pyrones via 3-hydroxyalkenyl phenyl sulfides

A diastereodivergent synthesis of optically active trans- and cis-6-benzyloxymethyl-4-hydroxytetrahydro-2-pyrones has been developed via 3-hydroxyalkenyl phenyl sulfides by employing base-induced cleavage of the glycidyl phenyl sulfide functionality as th