186378-98-3

Upstream product

• 196861-67-3 Toluene-4-sulfonic acid (2S,4S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl ester 
• 103708-37-8 (2S,4S)-4-hydroxymethyl-2-(p-methoxymethyl)-1,3-dioxane 
• 196861-72-0 (2S,4S)-2-(4-Methoxy-phenyl)-4-phenylsulfanylmethyl-[1,3]dioxane 
• 6290-03-5 (R)-butane-1,3-diol 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 6290-03-5 (R)-butane-1,3-diol 

Relevant academic research and scientific papers

Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments

Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-6a which formed respectively in these conditions have been converted efficiently into the title fragments of spiramycin.

Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (R)-1,3-Butanediol

In the presence of a catalytic amount (0.1-0.2 molar amount) of a 2-phenyl-1,3,2-oxazaborolidin-5-one, prepared by the reaction of dichlorophenylborane and N-(trifluoromethylsulfonyl)-L- phenylalanine, and enol silyl ethers ((R2)2C=C-(R3)OTMS; R3 = t-BuS, EtS, EtO, Ph) (1.1-1.5 molar amount), chiral cyclic acetals 6 derived from (R)-1,3-butanediol and aldehydes undergo an efficient ring-cleavage reaction with the inversion of the stereochemistry at the acetal carbon to give the anti isomer of the corresponding products with high stereoselectivity. The reaction is applicable to acetals derived from aromatic, aliphatic, and α,β-unsaturated aldehydes. Not only enol silyl ethers, but also methallyltrimethylsilane and allyltributyltin, can be employed as nucleophiles, leading to the selective formation of the anti isomer of the corresponding allylated ring-cleavage products. Removal of the chiral auxiliary from these ring-cleavage products by a two-step sequence ((i) PCC (ii) Bn2NH2(CF3CO2)) furnishes enantiomerically enriched β-hydroxy carbonyl compounds and homoallyl alcohols. A modest level of kinetic resolution is observed in the ring cleavage of a racemic acetal catalyzed by a phenylboron compound derived from N-mesyl-L-phenylalanine.