116003-84-0

Upstream product

• 127665-77-4 (E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol 
• 127047-71-6 3-(tert-butyldiphenylsilyloxy)propan-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 162473-68-9 methyl 5-(tert-butyldiphenylsilyl)oxy-2-pentenoate 
• 1195778-61-0 C₂₉H₄₁NO₄SSi 
• 88158-68-3 4-(tert-butyldiphenylsilyloxy)-1-butyne 
• 88159-03-9 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol 
• 656238-49-2 (E)-5-(tert-Butyl-diphenyl-silanyloxy)-pent-2-en-1-ol 
• 135006-32-5 4-tert-butyldiphenylsilyloxy-1-butene 
• 256494-25-4 (E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 

Downstream Products

• 142204-71-5 (2S,3R)-3-benzoyloxy-5-tert-butyldiphenylsilyloxy-1,2-pentanediol 
• 256494-32-3 (2R,3S)-3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)oxirane-2-carbaldehyde 
• 671232-56-7 tert-Butyl-diphenyl-[2-((2S,3S)-3-trityloxymethyl-oxiranyl)-ethoxy]-silane 
• 920502-51-8 (2S,3R)-1,2-dihydro-5-tertbutyldiphenylsilyloxy-pentan-3-yl 2-(phenylthio)acetate 
• 920502-63-2 (3S,4R,5R)-4,5-diallyl-3-phenylthio-dihydrofuran-2-one 
• 920502-62-1 (3S,4R,5R)-4-allyl-5-(2-hydroxyethyl)-3-phenylthio-dihydrofuran-2-one 
• 920502-58-5 (3S,4R,5R)-4-allyl-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one 
• 920502-57-4 (3S,4R,5R)-4-(2-hydroxy-ethyl)-3-phenylthio-5-(2-tert-butyldiphenylsilyloxy)ethyl-dihydrofuran-2-one 
• 920502-56-3 (2R,3R,4S)-[5-oxo-4-(phenylthio)-2-(2-tert-butyldiphenylsilyloxy)ethyl-tetrahydrofuran-3-yl]acetic acid 
• 162264-90-6 Methyl (2R,3R,4S)-<5-oxo-4-(phenylthio)-2-<2-<(tert-butyldiphenylsilyl)oxy>ethyl>tetrahydrofuran-3-yl>acetate 
• 671232-54-5 2-((2S,3S)-3-Trityloxymethyl-oxiranyl)-ethanol 
• 126616-47-5 (R)-(-)-4-tert-butyldiphenylsilyloxy-1-methylbutanal 
• 126616-33-9 (R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-butyryl chloride 
• 142387-16-4 (R)-4-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-butyramide 

Relevant academic research and scientific papers

Concise Seven-Membered Oxepene/Oxepane Synthesis - Structural Motifs in Natural and Synthetic Products

This work outlines a suitable method for the synthesis of oxepane skeleton using iterative C-glycoside technology on the oxepene intermediate, which was synthesized utilizing Wilkinson's catalyst [Rh(PPh 3) 3 Cl] to generate the isom

Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar

Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral v

First stereoselective total synthesis of decarestrictine O via RCM protocol

A convergent first stereoselective total synthesis of decarestrictine O via RCM protocol starting from 1,3-propanediol and propylene oxide is reported.

A highly efficient methodology of asymmetric epoxidation based on a novel chiral sulfur ylide

A new type of chiral sulfur ylides has been synthesized and their reactivities against carbonyl compounds tested, showing a high degree of stereoselectivity in the formation of trans epoxy amides under very mild reaction conditions.

Divergent syntheses of resorcylic acid lactones: L-783277, LL-Z1640-2, and hypothemycin

The resorcylic acid lactones (RAL) are endowed with diverse biological activity ranging from transcription factor modulators (zearalenone and zearalenol) to HSP90 inhibitors (radicicol and pochonin D) and reversible (aigialomycin D) as well as irreversibl

Total syntheses of amphidinolide X and Y

Concise total syntheses of the cytotoxic marine natural products amphidinolide X (1) and amphidinolide Y (2) as well as of the nonnatural analogue 19-epi-amphidinolide X (47) are described. A pivotal step of the highly convergent routes to these structurally rather unusual secondary metabolites consists of a syn-selective formation of allenol 17 by an iron-catalyzed ring opening reaction of the enantioenriched propargyl epoxide 16 (derived from a Sharpless epoxidation) with a Grignard reagent. Allenol 17 was then cyclized with the aid of Ag(I) to give dihydrofuran 19 containing the (R)-configured tetrasubstituted sp3 chiral center at C. 19, which was further elaborated into tetrahydrofuran 25 representing the common heterocyclic motif of 1 and 2. The aliphatic chain of amphidinolide X featuring an anti-configured stereodiad at C. 10 and C. 11 was generated by a palladium-catalyzed, Et 2Zn-promoted addition of the enantiopure propargyl mesylate 29 to the functionalized aldehyde 28. The preparation of the corresponding C.1-C.12 segment of amphidinolide Y relies on asymmetric hydrogenation of an α-ketoester, a diastereoselective boron aldol reaction, and a chelate-controlled addition of MeMgBr in combination with suitable oxidation state management for the elaboration of the tertiary acyloin motif. Importantly, the end games of both total syntheses follow similar blueprints, involving key fragment coupling processes via the "9-MeO-9-BBN" variant of the alkyl-Suzuki reaction and final Yamaguchi esterifications to forge the 16-membered macrodiolide ring of amphidinolide X and the 17-membered macrolide frame of amphidinolide Y, respectively. This methodological convergence ensures high efficiency and an excellent overall economy of steps for the entire synthesis campaign.

Enantioselective Synthesis and Biological Activity of (3S,4R)- and (3S,4S)-3-Hydroxy-4-hydroxymethyl-4-butanolides in Relation to PGE2

Compounds 9 and 13 were synthesized, and their structures and stereochemistry were elucidated by spectroscopic methods. In competition binding experiments, specific [3H]-PGE2 binding was significantly displaced by compound 9 and, to a lesser extent, by 13, in a dose-dependent manner. The biological properties of compound 9 were studied on HL-60 cells, and several effects were found related to those of PGE 2. Compound 9 increases c-fos mRNA level as does PGE2 and antagonizes TPA-induced terminal differentiation.

Total synthesis of amphidinolide X

A concise total synthesis of the cytotoxic marine natural product amphidinolide X (1) is described. A key step of the highly convergent route to this structurally rather unusual macrodiolide derivative consists of a newly developed, highly syn selective f

Synthesis of chiral 4-hydroxy-2,3-unsaturated carbonyl compounds from 3,4-epoxy alcohols by oxidation: Application in the formal synthesis of macrosphelide A

An interesting transformation during the oxidation of 3,4-epoxy alcohols 1a-d, derived from the corresponding homoallylic alcohols, led to the formation of 4-hydroxy-2,3-unsaturated carbonyls 2a-d in very good yields. One of these products 2c was transfor

Synthetic studies on pectenotoxins: Synthesis of the common C8-C18 THF fragment

The stereoselective synthesis of the common C8-C18 THF fragment of pectenotoxins is reported. The THF ring was constructed by the ring closure of the epoxide possessing all six asymmetric centers with a 5-exo-mode. These stereogenic centers were arranged successively from the enantiomerically active epoxide by utilizing the stereo-differentiating influence of the proximal functional groups.