104784-02-3Relevant articles and documents
Indium-mediated cleavage of the trityl group from protected alcohols and diols
Behloul, Cherif,Chouti, Aicha,Guijarro, David,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
, p. 7937 - 7941 (2016/11/19)
The reaction of primary, secondary, allylic and benzylic trityl ethers with indium powder in MeOH/NH4Cl led to reductive cleavage of the trityl-oxygen bond, affording the corresponding alcohols in good to excellent yield under very mild reaction conditions. The detritylation process could successfully be extended to mono and detritylated diols. This methodology represents a new and efficient detritylation procedure under mild reaction conditions.
Convergent syntheses of 3,6-dihydroxydec-4-enolides
Killen, Jonathan C.,Axford, Lorraine C.,Newberry, Sarah E.,Simpson, Thomas J.,Willis, Christine L.
supporting information; experimental part, p. 4194 - 4197 (2012/10/08)
The total syntheses of the 3,6-dihydroxydecanolide from Cordyceps militaris and the novel C-3 epimer are reported using a diastereoselective Nozaki-Hiyama-Kishi reaction in the key cyclization to generate the 6R stereocenter.
Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water
Shi, Lei,Liu, Yingying,Liu, Qingfeng,Wei, Bin,Zhang, Guisheng
experimental part, p. 1372 - 1375 (2012/06/04)
Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as a reducing agent. The procedure is also compatible with the presence of a variety of base-labile protecting groups, such as tosyl, acetyl, benzoyl, ester groups, and acid-labile protecting groups such as trityl and TBDMS groups, and others, such as the unsaturated double bond, nitro and cyano groups. Finally, a kilo scale reaction of methyl benzoylformate with AB was conducted in water and gave methyl mandelate in 94% yield.
Total synthesis of dolatrienoic acid: A subunit of dolastatin 14
Moune,Niel,Busquet,Eggleston,Jouin
, p. 3332 - 3339 (2007/10/03)
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.
SYNTHESIS OF THE PROPIONATES OF (2R,8R)- AND (2RS,8R)-8-METHYL-2-DECANOL, THE ATTRACTANTS OF THE WESTERN CORN ROOTWORM
Carpita, Adriano,Chini, Marco,Rossi, Renzo
, p. 29 - 34 (2007/10/02)
The propionate of (2R,8R)-8-methyl-2-decanol, (2R,8R)-1, an attractant of the western corn rootworm, Diabrotica virgifera Le Conte, has been prepared by a synthetic route in which enantiomerically pure methyl hydrogen (R)-3-methylglutarate, (R)-2, and (S)-glutamic acid, (S)-3, have been used as chiral precursors.In this convergent synthesis, (R)-2 and (S)-3 have been stereospecifically converted into (R)-1-bromo-3-methylpentane, (R)-4, and (R)-1,4-pentanediol, (R)-5, respectively.An analogous synthetic scheme has been followed to prepare biologically active (2RS, 8R)-1 starting from (R)-4 and racemic 5.
SYNTHESIS AND CHARACTERIZATION OF 4-DIMETHYLAMINO-N-TRIPHENYLMETHYLPYRIDINIUM CHLORIDE, A POSTULATED INTERMEDIATE IN THE TRITYLATION OF ALCOHOLS
Hernandez, O.,Chaudhary, S. K.,Cox, R. H.,Porter, J.
, p. 1491 - 1494 (2007/10/02)
4-Dimethylamino-N-triphenylpyridinium chloride (1) reacts with primary but not secondary alcohols to produce trityl ethers in good yield; in addition, amines may be selectively N-tritylated with 1 in the presence of alcohols.
