127758-12-7

Upstream product

• 127665-77-4 (E)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 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 
• 1438398-97-0 C₂₉H₄₁NO₄SSi 
• 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 
• 162473-68-9 methyl 5-(tert-butyldiphenylsilyl)oxy-2-pentenoate 
• 127047-71-6 3-(tert-butyldiphenylsilyloxy)propan-1-ol 
• 112897-03-7 3-(tert-butyldiphenylsilyloxy)-1-propanal 

Downstream Products

• 256494-33-4 (2S,3R)-3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)oxirane-2-carbaldehyde 
• 256494-32-3 (2R,3S)-3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)oxirane-2-carbaldehyde 
• 256494-42-5 (3R,4R,5R)-tert-butyl 3-(3-(2-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)ethyl)(2-oxiranyl))-3-hydroxypropanoate 
• 115946-43-5 (3R,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-1-(toluene-4-sulfonyl)-azetidin-2-one 
• 115946-39-9 (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-1-(toluene-4-sulfonyl)-aziridine 
• 115946-42-4 (2R,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-3-(toluene-4-sulfonylamino)-pentanoic acid 
• 115946-40-2 [(2S,3R)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanol 
• 115946-41-3 N-{(1R,2R)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2-hydroxymethyl-butyl}-4-methyl-benzenesulfonamide 
• 115946-44-6 (3R,4R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-3-ethyl-azetidin-2-one 
• 326471-56-1 (3S,4S)-3-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-4-(4-methoxy-benzyloxy)-hexan-2-one 
• 826994-86-9 tert-butyl(diphenyl){2-[(2S,3S)-3-(prop-1-ynyl)oxiran-2-yl]ethoxy}silane 
• 826994-85-8 tert-butyl{2-[(2S,3S)-3-ethynyloxiran-2-yl]ethoxy}diphenylsilane 
• 115946-38-8 (2S,3R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-3-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-aziridine 

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

A highly stereoselective synthesis of glycidic amides based on a new class of chiral sulfonium salts: Applications in asymmetric synthesis

A new type of chiral sulfonium salts that are characterized by a bicyclic system has been designed and synthesized from α-amino acids. Their corresponding ylides, which were prepared by basic treatment of the sulfonium salts, reacted smoothly with a broad array of simple and chiral aldehydes to provide trans-epoxy amides in reasonable to very good yields and excellent stereoselectivities (>98 %). The obtained epoxy amides were found to be useful as synthetic building blocks. Thus, they were reduced into their corresponding epoxy alcohols and subjected to oxirane-ring-opening reactions with different types of nucleophiles.

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.

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

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.

Attempt to rationalize the diastereoselectivity in the addition of ester enolate to optically active α,β-epoxyaldehydes

Aldol condensations on α,β-epoxyaldehyde having a remote alkoxy group have been realized. A rationalization of the outcome of this condensation is discussed, relying on the dominant conformers revealed by molecular modeling of anti and syn γ,δ-epoxy β-hyd

Die Struktur von Maitotoxin - II: Konfiguration der C135-C142-Seitenkette und absolute Konfiguration des gesamten Molekuels

Keywords: Asymmetrische Synthesen; Strukturaufklaerung; Maitotoxin; Naturstoffe; NMR-Spektroskopie