60656-87-3

Usage

Uses

Used in Pharmaceutical Industry:
Benzyloxyacetaldehyde is used as an acceptor for the engineering of 2-deoxyribose 5-phosphate aldolase variants, which are crucial in the enzymic preparation of β-ketols. This application is significant for the development of novel pharmaceutical compounds and the enhancement of existing drug synthesis processes.
Used in Chemical Synthesis:
Benzyloxyacetaldehyde serves as a key intermediate in the synthesis of various complex organic compounds, such as (3S,5S)-methyl 6-benzyloxy-3,5-dihydroxyhexanoate, (S)-5-benzyloxy-4-hydroxypentan-2-one, and myxothiazols. These synthesized compounds have potential applications in different fields, including pharmaceuticals, agrochemicals, and materials science.
Used in Research and Development:
Due to its unique chemical properties and reactivity, benzyloxyacetaldehyde is also utilized in research and development for the exploration of new synthetic pathways, the study of enantioselective reactions, and the development of novel catalysts and methodologies in organic chemistry.

InChI:InChI=1/C9H10O2/c10-6-7-11-8-9-4-2-1-3-5-9/h1-6H,7-8H2

Upstream product

• 31600-43-8 methyl 2-(benzyloxy)acetate 
• 622-08-2 2-Benzyloxyethanol 
• 68972-96-3 (Z)-1,4-dibenzyloxy-2-butene 
• 100791-51-3 (2R,3R,4R)-1-Benzyloxy-4-methyl-5-hexene-2,3-diol 
• 30379-55-6 benzyloxyacetic acid 
• 69010-01-1 (2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol 
• 796077-38-8 benzyloxy-acetic acid butyl ester 
• 70677-94-0 1,4-di(benzyloxy)but-2,3-ene 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 100-51-6 benzyl alcohol 
• 99878-63-4 4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose 
• 20194-18-7 sodium phenyl-methanolate 
• 75-09-2 dichloromethane 

Downstream Products

• 14869-00-2 1-(benzyloxy)butan-2-ol 
• 854724-08-6 3-benzyloxy-1-cyclohex-1-enyl-1-nitro-propan-2-ol 
• 62987-20-6 3'-benzyloxymethyl-1'-thioxo-2',3',6',7'-tetrahydro-1'H-spiro[[1,3]dioxane-2,5'-pyrrolo[1,2-c]pyrimidine]-4'-carboxylic acid methyl ester 
• 71841-10-6 (E)-2-(2-Benzyloxy-1-hydroxy-ethyl)-6,10-dimethyl-2-phenylsulfanyl-undeca-5,9-dienoic acid methyl ester 
• 66646-70-6 2-amino-4-benzyloxy-3-hydroxy-butyric acid methyl ester 
• 65577-51-7 [1-(Benzhydryl-amino)-2-benzyloxy-ethyl]-phosphinic acid 
• 70350-62-8 phosphonylethanolamine 
• 101062-05-9 2-benzyloxy-N-(2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl)ethanimine 
• 70150-60-6 ethyl 2E-4-(benzyloxy)-2-butenoate 
• 157542-41-1 (2R,3R)-1-benzyloxy-3-methyl-4-penten-2-ol 
• 80127-39-5 2-benzyloxymethyl-2,3-dihydropyran-4-one 
• 133281-03-5 5-Heptadecyl-2-benzyloxymethyl-1,3-dioxolane 
• 84304-03-0 5-Benzyloxymethyl-4-bromo-5H-furan-2-one 
• 131991-73-6 (2R,6R)-2--6-methyl-1,3-dioxan-4-one 

Relevant academic research and scientific papers

Exploring the dNTP -binding site of HIV-1 reverse transcriptase for inhibitor design

HIV-1 reverse transcriptase (RT) plays a central role in the viral life cycle, and roughly half of the FDA-approved anti-HIV drugs are targeting RT. Nucleoside analogs (NRTIs) require cellular phosphorylation for binding to RT, and to bypass this rate-limiting path, we designed a new series of acyclic nucleoside phosphonate analogs as nucleoside triphosphate mimics, aiming at the chelation of the catalytic Mg2+ ions via a phosphonate and/or a carboxylic acid group. Novel synthetic procedures were developed to access these nucleoside phosphonate analogs. X-ray structures in complex with HIV-1 RT/dsDNA demonstrated that their binding modes are distinct from that of our previously reported compound series. The impact of chain length, chirality and linker atom have been discussed. The detailed structural understanding of these new compounds provides opportunities for designing new class of HIV-1 RT inhibitors.

Bio-derived nanosilica-anchored Cu(II)-organoselenium complex as an efficient retrievable catalyst for alcohol oxidation

A new copper(II) complex supported onto rice-husk-derived nanosilica was prepared from 2,6-bis((phenylselanyl)methyl)pyridine, salicylaldehyde and copper acetate monohydrate, Cu(OAc)2·H2O. The as-synthesized complex Cu(II)SeNSe@imine-nanoSiO2 (Complex I) was extensively characterized with FT-IR, powder XRD, SEM-EDX, solid-state UV-Vis, ESR, XPS, TGA and BET surface area analysis. The catalytic activity of the complex was explored for alcohol oxidation reactions using H2O2 as oxidant and acetonitrile as solvent. For comparison, we have also prepared an analogous homogeneous catalyst (Complex II) and characterized it with FT-IR, UV-Vis, LC-MS and ESR analyses. Its catalytic activity was also screened to the same reaction. The immobilized catalyst showed better efficiency with 75%–95% isolated yield compared with the homogeneous one for alcohol oxidation with at least five times recyclability without profound loss in activity.

3-(5-METHOXY-1-OXOISOINDOLIN-2-YL)PIPERIDINE-2,6-DIONE DERIVATIVES AND USES THEREOF

The present disclosure relates to compounds of formula (I') and pharmaceutical compositions and their use in reducing Widely Interspaced Zinc Finger Motifs (WIZ) expression levels, or inducing fetal hemoglobin (HbF) expression, and in the treatment of inherited blood disorders (e.g., hemoglobinopathies, e.g., beta-hemoglobinopathies), such as sickle cell disease and beta-thalassemia.

General Asymmetric Synthetic Strategy for the α-Alkylated 2,5,6-Trisubstituted Pyran of Indanomycin and Related Natural Products

A general synthetic strategy for convergent asymmetric synthesis of C1–C10 fragment of tetraene-containing natural product indanomycin was achieved starting from 2-(benzyloxy)acetaldehyde which in turn was obtained from very inexpensive material cis-1,4-butene-diol. Key steps include Evans' aldol reaction, HWE olefination, iodine-catalyzed tandem isomerization followed by C–O and C–C bond formation similar to our earlier report in constructing the trans-2,6-disubstituted dihydropyran ring and Evans' asymmetric alkylation.

SPIRO-LACTAM NMDA RECEPTOR MODULATORS AND USES THEREOF

Disclosed are compounds having potency in the modulation of NMDA receptor activity. Such compounds can be used in the treatment of conditions such as depression and related disorders as well as other disorders.

Correction to: Nickel-catalyzed asymmetric reductive cross-coupling to access 1,1-diarylalkanes (Journal of the American Chemical Society (2017) 139 (5684-5687) DOI: 10.1021/jacs.7b01705)

Pages 5684 and 5685, Table of Contents, and Supporting Information. The stereochemistry of L1, depicted as the (S,S)- enantiomer in Figure 1, Table 1, the TOC graphic (identical to Figure 1), and the Supporting Information of the original publication, was incorrect. (R,R)-L1 was used in this study. The stereochemistry of (R,R)-L1 has been confirmed by singlecrystal X-ray diffraction; the X-ray diffraction data and CIF file for (R,R)-L1 have been added to the Supporting Information. The corrected TOC graphic/Figure 1 is shown here. (R,R)-L4 and (R,R)-L5 were also used in Table 1 and incorrectly depicted as (S,S)-L4 and (S,S)-L5 in the original publication. To reflect that different enantiomeric series of catalysts were used, Table 1 has been updated to indicate that entries 2, 3, and 6 produce (S)-3a. This correction does not change the stereochemical assignment of the diarylalkane products, or the conclusions of the Communication. The stereochemistry of the products was assigned by obtaining an X-ray structure of diarylalkane 3k, and the rest of the compounds were assigned by analogy. (Table Presented).

Novel compound 6,6-dimethyl tetrahydropyran-2-methanol and preparing method thereof

The invention discloses a novel compound that is 6,6-dimethyl tetrahydropyran-2-methanol and a preparing method thereof. The method includes preparing benzyloxy ethanol by utilizing a sodium alkoxideprocess; then oxidizing the benzyloxy ethanol into benzyloxy acetaldehyde by utilizing a swern oxidation process; reacting the benzyloxy acetaldehyde and allyltributyltin prepared by utilizing a Grignard reaction to obtain 1-(benzyloxy)-4-penten-2-ol; subjecting the 1-(benzyloxy)-4-penten-2-ol and acetone to cyclization under catalysis of trimethylchlorosilane and potassium iodide to obtain 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol; and subjecting the 4-iodo-6,6-dimethyl tetrahydropyran-2-methanol to hydrogenation to remove iodine to obtain the target product that is the 6,6-dimethyl tetrahydropyran-2-methanol. According to the method, reactions are relatively mild, products can be easily treated and purified, and the method is suitable for batch preparation, and therefore the methodhas important application value.

Electrophile-Dependent Alkylations of Lithiated 4-Alkoxyalk-4-enenitriles

Alkylations of acyclic, lithiated 4-alkoxyalk-4-enenitriles are highly diastereoselective with an unusual electrophile-dependent preference. Alkyl halides, sulfur, chlorine, and acyl cyanide electrophiles intercept a series of lithiated 4-alkoxyalk-4-enenitriles to install contiguous tertiary-quaternary stereocenters with high diastereoselectivity, whereas acylations with ester and carbonate electrophiles are modestly selective. The diastereoselectivity is consistent with electrophilic attack on the most accessible face of the lithated nitrile for most electrophiles except ester and carbonate electrophiles, which likely precoordinate the lithiated nitrile before acylation. Intercepting the lithiated 4-alkoxyalk-4-enenitriles with a range of electrophiles provide insight into the criteria for otherwise challenging diastereoselective alkylations and acylations of acyclic nitriles.

Preparation method of rosuvastatin calcium medicine intermediate

The invention belongs to the technical field of medicine chemicals, and particularly relates to a preparation method of a rosuvastatin calcium medicine intermediate. The preparation method comprises the following steps of using monochloroacetaldehyde as the raw material; substituting, condensing, and chirally catalyzing, so as to prepare a compound V; protecting by 2,2-dimethoxypropane, and debenzylating, so as to obtain a target compound I. The preparation method has the advantages that the raw materials are easy to obtain; (S)-5-benzyl-2,2,3-trimethyl-4-thioketone is used as a catalyst for stereo selective reduction, the reaction conditions are mild, the yield rate is higher, and the industrialization production of the component I is easy.

Nickel-Catalyzed Asymmetric Reductive Cross-Coupling to Access 1,1-Diarylalkanes

An asymmetric Ni-catalyzed reductive cross-coupling of (hetero)aryl iodides and benzylic chlorides has been developed to prepare enantioenriched 1,1-diarylalkanes. As part of these studies, a new chiral bioxazoline ligand, 4-heptyl-BiOX (L1), was developed in order to obtain products in synthetically useful yield and enantioselectivity. The reaction tolerates a variety of heterocyclic coupling partners, including pyridines, pyrimidines, indoles, and piperidines.