838-66-4

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 100-52-7 benzaldehyde 
• 109-72-8 n-butyllithium 
• 110935-06-3 Butyltellanylmethoxymethyl-benzene 
• 93-56-1 phenylethane 1,2-diol 
• 620-05-3 iodomethylbenzene 
• 96-09-3 styrene oxide 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 4358-87-6 (RS)-methyl mandelate 
• 100-39-0 benzyl bromide 
• 60656-87-3 benzyloxyacetoaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 64904-47-8 2-benzoyloxyacetaldehyde 
• 108-86-1 bromobenzene 

Downstream Products

• 103394-86-1 2-(benzyloxy)-1-phenylethan-1-one 
• 93-56-1 phenylethane 1,2-diol 

Relevant academic research and scientific papers

A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates

Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

IDO inhibitors

Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism

As an extension of our previous research on the regioselective protection of carbohydrates and diols, we developed an iron catalyst, Fe(dibm)3 (dibm = diisobutyrylmethane), which has an unusually broad catalytic scope in the selective monoalkyl

Zirconium triflate grafted on SBA-15 as a highly efficient solid acid catalyst for ring opening of epoxides by amines and alcohols

Metal (Al, Ti, Zr) triflate grafted mesoporous SBA-15 (AlTf/S, TiTf/S, ZrTf/S) samples were synthesized as inexpensive solid acid materials by a simple one-pot-two-step synthesis methodology. These materials were characterized by X-ray diffraction, N2-sorption, thermogravimetric analysis, Fourier transform infrared spectroscopy (FT-IR), in-situ pyridine FT-IR spectroscopy, and elemental analysis. ZrTf/S was found to be a highly efficient and reusable solid acid catalyst for ring opening of epoxides with amines and alcohols and produced β-amino alcohols and β-alkoxy alcohols respectively under ambient reaction conditions. The ZrTf/S catalyst showed the highest activity, which was attributed to its high acidity compared with that of the Ti and Al containing samples.

An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols

In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.

A photochemical strategy for lignin degradation at room temperature

The development of a room-temperature lignin degradation strategy consisting of a chemoselective benzylic oxidation with a recyclable oxidant ([4-AcNH-TEMPO]BF4) and a catalytic reductive C-O bond cleavage utilizing the photocatalyst [Ir(ppy)2(dtbbpy)]PF6 is described. This system was tested on relevant lignin model substrates containing β-O-4 linkages to generate fragmentation products in good to excellent yields.

Regioselective benzylation of diols and polyols by catalytic amounts of an organotin reagent

An efficient one-pot method for the selective benzylation of diols and polyols using 0.1 equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis-vicinal diol were regioselectively

Copper(I)-catalyzed asymmetric desymmetrization: Synthesis of five-membered-ring compounds containing all-carbon quaternary stereocenters

A highly stereoselective catalytic alkylation sequence for the synthesis of highly functionalized and versatile five-membered-ring compounds bearing all-carbon quaternary stereocenters was developed. Enantioselective desymmetrization of achiral cyclopentene-1,3-diones was thus executed by chiral Cu-phosphoramidite catalysts. A variety of complicated cyclopentane derivatives can be synthesized with excellent stereoselectivities using a low catalyst loading in a one-pot operation.