83816-49-3

Upstream product

• 98-01-1 furfural 
• 624-65-7 2-propynyl chloride 
• 53915-69-8 allenyltributylstannane 
• 848617-96-9 (+/-)-B-allenyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 
• 90-82-4 rac-pseudoephedrine 
• 7487-94-7 mercury (II) chloride 
• 106-96-7 propargyl bromide 
• 848617-98-1 (10S)-B-allenyl-10-trimethylsilyl-9-borabocyclo[3.3.2]decane 
• 90-82-4 pseudoephedrine 

Downstream Products

• 1257108-86-3 (2E)-5-(furan-2-yl)-5-hydroxy-3-methoxy-2-pentenoic acid methyl ester 
• 78440-83-2 4-methoxy-6-(2-furyl)-5,6-dihydro-2-pyrone 

Relevant academic research and scientific papers

Asymmetric synthesis of homopropargylic alcohols from aldehydes and allenyltri-n-butylstannane

The reaction of allenyltri-n-butylstannane with aldehydes and a chiral Lewis acid prepared from (R)-BINOL and Ti(O-i-Pr)4 gives homopropargylic alcohols with 82 - > 99% ee

Nonracemic homopropargylic alcohols via asymmetric allenylboration with the robust and versatile 10-TMS-9-borabicyclo[3.3.2]decanes

(Chemical Equation Presented) The asymmetric allenylboration of representative aldehydes with the stable, storable 1 is reported. Easily and efficiently prepared in either enantiomeric form from the air-stable crystalline 4 through simple Grignard procedures, 1 gives 6 cleanly. The latter is easily isolated in high yield and ee with predictable stereochemistry. The procedure also regenerates 4 for its direct conversion back to 1 and facilitates the efficient recovery of the pseudoephedrine. The net process is the synthetic equivalent of the asymmetric addition of allenylmagnesium bromide to aldehydes.

Catalytic propargylation of aldehydes with allenyltributylstannane by ytterbium triflate

The first ytterbium triflate [Yb(OTf)3]-catalyzed propargylation of various aldehydes with allenyltributylstannane to afford homopropargyl alcohols in good yields is described. The present result provides a versatile tool for preparation of an array of homopropargyl alcohols from the reaction of aldehydes with allenyltributylstannane; which are known to possess low reactivity.

Zinc Barbier reaction of propargyl halides in water

The reaction of propargyl halides and carbonyl compounds with zinc powder proceeds in concentrated aqueous salt solutions affording with high selectivity homopropargylic alcohols preparatively useful yields are obtained with aromatic and aliphatic aldehydes. Ketones and 2-hydroxybenzaldehydes react partially. A surface process of two SET is discussed.

Allenic prostanoic acid derivatives

This invention relates to novel allenic prostanoic acid derivatives having the following formula STR1 wherein R is hydrogen; or straight or branched chain alkyl of 1 to 6 carbon atoms, inclusive wherein R1 is hydrogen; or straight or branched chain alkyl of 1 to 6 carbon atoms, inclusive; or vinyl (--CH=CH2) wherein R2 is straight or branched chain alkyl of 1 to 6 carbon atoms; or cycloalkyl group containing 3 to 6 carbon atoms; or phenyl; or phenoxy wherein R3 is hydrogen; or straight chain alkyl of 1 to 3 carbon atoms wherein m is an integer of from 1 to 4, inclusive, wherein n is an integer of from 1 to 3, inclusive with the proviso that the sum of m and n does not exceed 5, wherein y is an integer of from 1 to 3. These compounds are useful by reason of their gastric antisecretory and cytoprotective activity.

3-Oxaprostaglandins

This invention relates to novel 3-oxa-15-desoxy-16-hydroxy-16-alkyl prostaglandins of the E2 series and the 5,6-acetylene derivatives thereof. These compounds are useful for their gastric antisecretory, cytoprotective, antiulcer, and antihypertensive activity. In addition the invention also discloses certain novel trialkylsilyl acetylenic intermediates.