96481-69-5

Upstream product

• 92760-22-0 (S)-4-Benzyloxy-2-methyl-butyric acid methyl ester 
• 120810-79-9 2-((S)-3-Benzyloxy-1-methyl-propyl)-[1,3]dithiolane 
• 66261-30-1 (S)-4-(benzyloxy)-2-methylbutan-1-ol 
• 54555-84-9 benzyl iodoethyl ether 
• 120810-77-7 (2S,4S,5R)-4-Methyl-2-((S)-1-methyl-3-oxo-propyl)-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 120810-97-1 (2S,4S,5R)-2-((S)-3-Hydroxy-1-methyl-propyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 120810-78-8 (2S,4S,5R)-2-((S)-3-Benzyloxy-1-methyl-propyl)-4-methyl-5-phenyl-oxazolidine-3-carboxylic acid benzyl ester 
• 763-32-6 2-methyl-1-buten-4-ol 
• 63473-60-9 (S)-5-methoxy-3-methyl-5-oxopentanoic acid 
• 173209-00-2 (3S)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 
• 948859-72-1 (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester 
• 169897-87-4 [4S]-4-benzyl-3-(4-benzyloxy-1-butanoyl)-2-oxazolidinone 
• 10385-30-5 4-(benzyloxy)butanoic acid 
• 199472-02-1 (S,S)-5-benzyloxy-3-methyl-pentane-1,2-diol 

Downstream Products

• 96481-77-5 (S)-1-Benzyloxy-3-methyl-5-methylene-heptan-4-ol 
• 96481-74-2 (10S)-methyl 4,10-dimethyl-8-ethyl-12-(benzyloxy)dodeca-4(E),8(E)-dienoate 
• 96481-80-0 Benzoic acid (4E,8E)-(S)-1-[(2S,4R)-1-benzenesulfonyl-2-methyl-4-(2-methyl-[1,3]dioxolan-2-yl)-pentyl]-5-ethyl-11-methoxycarbonyl-3,9-dimethyl-undeca-4,8-dienyl ester 
• 99493-42-2 (S)-(+)-14-Methyl-1-octadecene 
• 27608-03-3 (R)-3-methylheptanal 
• 61169-84-4 (S)-3-methylheptan-1-ol 
• 943858-47-7 C₂₅H₃₁NO₅ 
• 96481-72-0 (E)-(S)-8-Benzyloxy-4-ethyl-6-methyl-oct-4-enoic acid methyl ester 

Relevant academic research and scientific papers

Enantioselective Synthesis of the Sex Pheromone of Lichen Moth, Miltochrista calamine, and Its Diastereomer

The synthesis of a Miltochrista calamine sex pheromone and its diastereomer has been developed. The key steps of the synthetic approach involved Evans' chiral auxiliaries and the addition of alkyne to aldehyde, which were firstly applied to prepare this sex pheromone and its diastereomer. The synthetic sex pheromone could be used to trap insects and study physiological and ecological questions of the lichen moth.

Total Synthesis of the Alleged Structure of Crenarchaeol Enables Structure Revision**

Crenarchaeol is a glycerol dialkyl glycerol tetraether lipid produced exclusively in Archaea of the phylum Thaumarchaeota. This membrane-spanning lipid is undoubtedly the structurally most sophisticated of all known archaeal lipids and an iconic molecule in organic geochemistry. The 66-membered macrocycle possesses a unique chemical structure featuring 22 mostly remote stereocenters, and a cyclohexane ring connected by a single bond to a cyclopentane ring. Herein we report the first total synthesis of the proposed structure of crenarchaeol. Comparison with natural crenarchaeol allowed us to propose a revised structure of crenarchaeol, wherein one of the 22 stereocenters is inverted.

A New Asymmetric Synthesis of (S)-14-Methyloctadec-1-ene, the Sex Pheromone of the Peach Leafminer Moth

Abstract: An asymmetric synthesis of 14-methyl-1-octadecene, the sex pheromone of thepeach leafminer moth has been achieved. Based on the asymmetric methylation ofchiral (S)-4-benzyloxazolidin-2-one, thecarbon chain of the target molecule was assembled through aC1+C10+C4+C3procedure. The γ-lactone was transformed into 4-(benzyloxy)butanoic acid andthen, with the induction of Evan’s template, a chiral methyl group wasintroduced to the position of the carboxylic group in 97percent de. After reduction and a couple of chemicaloperations, the designed key intermediate A1was obtained. The synthesis of another moiety was started from decane-1,10-diolwhich was selectively protected and oxidized. The long carbon chain wasinstalled according to a Wittig protocol. After deprotection, oxidization, andmethylenation, the target molecule was synthesized in 7 linear steps with anoverall yield of 30.3percent.

Synthesis, Profiling, and Bioactive Conformation of trans-Cyclopropyl Epothilones

A series of new 3-deoxy-C(12),C(13)-trans-cyclopropyl-epothilones have been prepared, bearing benzothiazole, quinoline, thiazol-5-ylvinyl, or isoxazol-3-ylvinyl side chains. For analogs with fused aromatic side chains, macrocyclic ring-closure was based on ring-closing olefin metathesis (RCM) of a precursor incorporating the fully elaborated heavy atom framework of the target structure (including the side chain moiety), while side chain attachment for the thiazole and isoxazole-containing 16-desmethyl analogs was performed only after establishment of the macrolactone core. Two approaches were elaborated for a macrocyclic aldehyde as the common precursor for the latter analogs that involved ring-closure either by RCM or by macrolactonization. Benzothiazole- and quinoline-based analogs were found to be highly potent antiproliferative agents; the two analogs with a thiazol-5-ylvinyl or an isoxazol-3-ylvinyl side chain likewise showed good antiproliferative activity but were significantly less potent than the parent epothilone A. Surprisingly, the desaturation of the C(10)?C(11) bond in these analogs was associated with a virtually complete loss in antiproliferative activity, which likely reflects a requirement for a ca. 60 ° C(10)?C(11) torsion angle in the tubulin-bound conformation of 12,13-trans-epothilones.

Total Synthesis of Biselyngbyolide B

The first total synthesis of biselyngbyolide B, an 18-membered macrolide, was achieved. The 18-membered ring structure was constructed by esterification using the Shiina reagent and an intramolecular Stille coupling reaction.

Synthesis of an A-E gambieric acid subunit with use of a C-glycoside centered strategy

This paper describes our synthesis of the A-E subunit of gambieric acid (GA) in addition to the synthesis of the A-ring and the C-E tricycle The use of an enol ether-olefin RCM strategy to couple the A and C-E subunits and, in the process, generate the B-

Synthetic studies toward potent cytotoxic agents amphidinolides: Synthesis of the C1-C18 moiety of amphidinolides G, H and L

Stereoselective synthesis of the (8S, 9S, 11R, 16S)-C1-C18 segment 1 of amphidinolides G, H and L, bearing the unique trisubstituted 's-cis-1,3- diene' moiety (C(28(29))=C13-C14=C15), has been achieved for the first time following a highly efficient convergent strategy.

ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION OF CUPRATES IN THE PRESENCE OF TRIMETHYLCHLOROSILANE. ENANTIOSELECTIVE SYNTHESIS OF 2-ALKYL-4-BENZYLOXYBUTANAL AND 2-ALKYL-4-OXOPENTANAL.

Cuprate reagents in the presence of trimethylchlorosilane add with excellent Π-face selectivity and yield to α,β-unsaturated ketone and aldehyde bearing in γ-position a masked aldehyde represented by the C-2 of a norephedrine-derived oxazolidine.The title

Synthesis of the Proposed Penultimate Biosynthetic Triene Intermediate of Monensin A

A convergent chiral synthesis of the putative biosynthetic triene precursor, 2b, has been accomplished.Our strategy entails the successive assembly of three key chiral synthons, prepared by enzymatic and microbial techniques.

BIFUNCTIONAL CHIRAL SYNTHONS VIA BIOCHEMICAL METHODS. VI. C5 ISOPRENOID UNITS.

Two methods for the preparation of the isoprenoid chiron 4 have been developed using a microbial kinetic resolution of 5 and an enantiotopically selective hydrolysis of 7 catalyzed by PLE.