87729-38-2

Upstream product

• 14273-92-8 methyl 5-hydroxypentanoate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 67-56-1 methanol 
• 288-32-4 1H-imidazole 

Downstream Products

• 149130-13-2 6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-one 
• 149130-14-3 (S)-6-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hexan-2-ol 
• 156764-06-6 1-[(R)-(S)-2,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexane-1-sulfinyl]-4-methyl-benzene 
• 70578-51-7 6-trans-Leukotriene B₄ 
• 817208-65-4 5-tert-butoxycarbonylamino-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-oxo-7-(tritylcarbamoyl)hept-2-enoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of a tripeptide derivative containing the Gln-Arg hydroxyethylene dipeptide isostere

(Chemical Equation Presented) The protected hydroxyethylene dipeptide isostere of Gln-Arg and the tripeptide derivative 1 were synthesized as components of potential peptidase inhibitors.

New insights into the reduction of β,δ-diketo-sulfoxides

New developments in the reduction of β,δ-diketo-sulfoxides, a reaction that affords important key intermediates for total synthesis, are described. We showed without ambiguity using NMR experiments, that the β-carbonyl group is totally enolised. This result is inconsistent with the previous hypothesis, which supposed the other tautomer (enolisation at the δ-position) as the major one. We propose a rationale to explain the side reactions occurring during the reduction of unprotected β,δ-diketo-sulfoxides and showed that judicious protection of the δ-carbonyl group gave all diastereoisomers of β-hydroxy-δ-ketosulfoxides.

Process for the manufacture of (6E)-leukotriene B4 and intermediates of the said manufacturing process

The invention relates to a process for the manufacture of 6-trans-leukotriene B4 (LTB4) of formula STR1 in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: STR2 the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB4. The invention also relates to intermediates obtained in the said manufacturing process.

ALKOXY RADICALS IN ORGANIC SYNTHESIS. A NOVEL APPROACH TO SPIROKETALS

Photolysis of an unsaturated alcohol in the presence of HgO and iodine generates an alkoxy radical which can cyclize to form a five-membered ring ether.If a hemiketal is employed, a spiroketal can be formed in good yield.

Rotational Selectivity in Cyclobutene Ring Openings. Model Studies Directed toward a Synthesis of Verrucarin A

The rotational selectivity in the opening of dissymmetric cyclobutenes to the corresponding dienes is described.In the opening of the monoesters of cis-3,4-cyclobutenedicarboxylic acid, an unusual solvent effect on the ring opening is noted.Switching from Me2SO to 1,2-dichloroethane leads to a 3:1 ratio of the (E,Z)-muconates, favoring the ester on the E double bond.The two isomers can be differentiated by 13C NMR spectroscopy in which the above isomer shows a Δδ for the α,α' carbons of only ca. 2.5 ppm but a Δδ of 5-6 ppm for the isomer having the ester on theZ double bond.Inclusion of the cyclobutene as part of a macrotriolide related to verrucarin A imparts conformational control on the rotational selectivity to favor the E,Z isomer corresponding to the natural products.These relatively simple models inhibit protein synthesis in a fashion reminiscent of the natural products.