138490-41-2

Upstream product

• 135067-28-6 2-((6R,7S,10R)-7-Isopropyl-10-methyl-1,5-dioxa-spiro[5.5]undec-2-yl)-ethanol 
• 98-59-9 p-toluenesulfonyl chloride 
• 4328-94-3 pentane-1,3,5-triol 
• 10458-14-7 (2R,5S)-menthone 
• 922-65-6 divinylcarbinol 
• 135067-24-2 3-(tert-butyldimethylsilanyloxy)pentane-1,5-diol 
• 74685-20-4 1,3,5-pentanetriol tris(trimethylsilyl) ether 
• 82865-59-6 3--1,4-pentadiene 

Relevant academic research and scientific papers

Total synthesis of dolatrienoic acid: A subunit of dolastatin 14

The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

Stereoselective Acetalization of 1,3-Alkanediols by l-Menthone: Application to the Resolution of Racemic 1,3-Alkanediols and to the Determination of the Absolute Configuration of Enantiomeric 1,3-Alkanediols

A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described.Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4.The two can be readily separated by silica gel column chromatography.Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol.An empirically derived correlation of configuration and 1H NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation.The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.