56850-58-9

Upstream product

• 72657-23-9 methyl (R)-3-hydroxy-2-methylpropionate 
• 409110-43-6 2,2,2-trichloro-acetimidic acid phenyl ester 
• 154201-91-9 methyl 2-((benzyloxy)methyl)acrylate 
• 7285-83-8 2,4,6-tris(benzyloxy)-1,3,5-triazine 
• 27691-43-6 1-(benzylsulphanyl)-4-Nitrobenzene 
• 67-56-1 methanol 
• 88729-00-4 (-)-(R)-3-benzyloxy-2-methylpropionic acid 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 40864-08-2 2-benzyloxypyridine 
• 882980-43-0 2-benzyloxy-1-methylpyridinium triflate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 

Downstream Products

• 122648-83-3 (R)-N,N-diethyl-6-<4-(benzyloxy)-3-methyl-2-oxobutyl>-2-methoxy-3-methylbenzamide 
• 63930-46-1 (S)-3-benzyloxy-2-methylpropan-1-ol 
• 185410-36-0 ((R)-4-Benzyloxy-3-methyl-2-methylene-butyl)-isopropoxy-dimethyl-silane 
• 192993-13-8 (2R)-1-benzyloxy-2-methylhexan-3-one 
• 79026-61-2 (R)-3-benzyloxy-2-methylpropanal 
• 88729-00-4 (-)-(R)-3-benzyloxy-2-methylpropionic acid 
• 246144-99-0 (R)-4-benzyloxy-1,1-dibromo-3-methylbutan-2-one 
• 565454-94-6 (S)-(4-(benzyloxy)-3-methyl-2-methylenebutyl)trimethylsilane 
• 934165-93-2 (2S,3S,4S,5S,8S)-9-benzyloxy-3-(4-methoxy-benzyloxy)-2,4,8-trimethyl-non-6-yne-1,5-diol 
• 934165-95-4 (2S,3S,4S,5R,8S)-9-benzyloxy-3-(4-methoxy-benzyloxy)-2,4,8-trimethyl-nonane-1,5-diol 
• 934165-99-8 C₃₉H₆₄O₅Si₂ 
• 934165-96-5 1-{(1S,2R,3R,6S)-7-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2,6-dimethyl-heptyloxymethyl}-4-methoxy-benzene 
• 934165-89-6 ((S)-2-methyl-but-3-ynyloxymethyl)-benzene 
• 944415-98-9 (2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol 

Relevant academic research and scientific papers

Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions

A sulfonium ylide participated alkylation and arylation under transition-metal free conditions is described. The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of wide variety of substrates including carbohydrates.

Ring-closing metathesis approaches towards the total synthesis of rhizoxins

Efforts are described towards the total synthesis of the bacterial macrolide rhizoxin F, which is a potent tubulin assembly and cancer cell growth inhibitor. A significant amount of work was expanded on the construction of the rhizoxin core macrocycle by ring-closing olefin metathesis (RCM) between C(9) and C(10), either directly or by using relay substrates, but in no case was ringclosure achieved. Macrocycle formation was possible by ring-closing alkyne metathesis (RCAM) at the C(9)/C(10) site. The requisite diyne was obtained from advanced intermediates that had been prepared as part of the synthesis of the RCM substrates. While the direct conversion of the triple bond formed in the ring-closing step into the C(9)-C(10) E double bond of the rhizoxin macrocycle proved to be elusive, the corresponding Z isomer was accessible with high selectivity by reductive decomplexation of the biscobalt hexacarbonyl complex of the triple bond with ethylpiperidinium hypophosphite. Radical-induced double bond isomerization, full elaboration of the C(15) side chain, and directed epoxidation of the C(11)-C(12) double bond completed the total synthesis of rhizoxin F.

Progress toward the total synthesis of mirabalin isomers

Key fragments of the cytotoxic marine macrolide mirabalin have been synthesized, by using a flexible strategy based on asymmetric reductions to control the hydroxy- and carbamate-bearing stereocenters. In particular, ruthenium or rhodium-mediated asymmetric hydrogenation and transfer hydrogenation were used in combination with a dynamic kinetic resolution to control two contiguous stereocenters in a single step.

Bombyx uterol ester (((R)-(-)-3-2- R) and its derivatives) and synthetic method thereof (by machine translation)

The invention discloses a synthetic method of ((R)- (-) - 3 - rhodanshi ester (R)-2-methyl) propionate (methyl propionate) and a derivative thereof. To the synthetic method disclosed by the (S)- 4 - invention, as a raw material, a series of reactions such as acylation, substitution, hydrolysis, esterification, hydrogenation and ((R)- (-) - 3 - the like are synthesized to synthesize the Rogoligoligoligoligosl)-methyl propionate and derivatives thereof. The synthesis method is equally applicable to the synthesis of its enantiomers and derivatives thereof. The method has the advantages of short reaction time, high yield, good chiral selectivity, suitability for industrial production and the like. The invention relates to a roshi ester and a derivative structure thereof. . (by machine translation)

Preparation of Alkyl Ethers with Diallyltriazinedione-Type Alkylating Agents (ATTACKs-R) Under Acid Catalysis

Diallyltriazinedione-type acid-catalyzed alkylating agents (ATTACKs-R) with 10 different alkyl groups (R), including benzyl, substituted benzyl, allyl, and methyl groups were synthesized. The palladium-catalyzed intramolecular O-to-N allylic rearrangement of 2,4-bis(allyloxy)-6-chloro-1,3,5-triazine was developed to introduce various alkoxy groups into the N,N′-dialkylated triazinedione skeleton. O-Alkylation of alcohols with ATTACKs-R was carried out in 1,4-dioxane in the presence of 2,6-di-tert-butylpyridinium trifluoromethanesulfonate or trifluoromethanesulfonic acid as a catalyst. Six selected ATTACKs-R bearing benzylic R groups were employed to prepare alkyl ethers from primary, secondary, and tertiary alcohols. The reactions of ATTACKs-R bearing an o-nitro-substituted benzyl group tended to afford low yields. Comparison of four different triazinedione-based benzylating reagents suggested that the N,N′-substituents affected the reactivity.

Development of triazine-based benzylating reagents possessing T-butyl group on the triazine core: Thermally controllable reagents for the initiation of reaction

Benzylating reagents, 4-(4,6-di-t-butyl-1,3,5-triazin-2-yl)-4-benzylmorpholinium triflate, and related derivatives have been developed. The reagents release benzyl triflate as a benzyl cation equivalent upon heating the solution to 40°C under neutral conditions. The O-benzylation of alcohols using a stoichiometric amount of these reagents afforded corresponding benzyl ethers in good to high yields. This was due to the presence of a bulky t-butyl group on the triazine ring of these reagents that prevents the consumption of benzyl triflate via a side reaction with a morpholinotriazine derivative.

N,N′-Dimethylated Benzyloxytriazinedione: A Stable Solid Reagent for Acid-Catalyzed O-Benzylation

N,N′-Dimethylated 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (DMBOT) has been developed as a triazinedione-based, stable solid reagent for acid-catalyzed O-benzylation. The conceptual basis of the design was to fix the core triazinedione skeleton, and

TRIAZINE DIONE COMPOUND

PROBLEM TO BE SOLVED: To provide a novel triazine dione compound useful as an alkylating agent for a nucleophilic compound. SOLUTION: This invention relates to a compound represented by formula (I) [where each symbol is as defined in the specification] and an alkylating agent comprising the compound, and a method for alkylating a nucleophilic compound using the alkylating agent. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT

Total synthesis of odoamide, a novel cyclic depsipeptide, from an Okinawan marine cyanobacterium

Odoamide is a novel cyclic depsipeptide with highly potent cytotoxic activity isolated from the Okinawan marine cyanobacterium Okeania sp. It contains a 26-membered macrocycle composed of a fatty acid moiety, a peptide segment and isoleucic acid. Four pos

Finding the Selectivity Switch - A Rational Approach towards Stereocomplementary Variants of the Ene Reductase YqjM

Ene reductases from the Old Yellow Enzyme family are versatile biocatalysts useful for the synthesis of optically active compounds. One disadvantage of biocatalysts when compared to competing catalysts in chemical syntheses is that often only one stereoisomer of the product is available. Another drawback can be the lack of activity in certain enzyme-substrate combinations. We were able to approach both of these challenges rationally in the case of the enzymatic synthesis of methyl 3-hydroxy-2-methylpropanoate (commonly denoted as the Roche ester) and derivatives thereof using the ene reductase YqjM. By a highly efficient, concept-based approach of designing mutant variants of YqjM and engineering substrates we could alter both the rate constant and the enantioselectivity of the reaction. Preparative scale reactions have been performed with successful mutants. In addition, the iterative modification of the substrate gave experiment-based insights into the binding mode of the Roche ester precursor and its derivatives.