1,2-cis-Selective glucosylation enabled by halogenated benzyl protecting groups

Literature Information

Publication Date 2020-03-10
DOI 10.1039/D0OB00373E
Impact Factor 3.876
Authors

Dancan K. Njeri, Claude J. Pertuit, Justin R. Ragains


View Original

Abstract

We report on our initial results from a systematic effort to implement electron-withdrawing protecting groups and Lewis basic solvents/additives as an approach to 1,2-cis(α)-selective O-glucosylation. 1,2-cis-Selective O-glucosylations are reported with thioglucosides and glucosyl trichloroacetimidates and a range of acceptors. A correlation between electron-withdrawing effects and 1,2-cis selectivity has been established. This phenomenon may prove to be broadly applicable in the area of chemical O-glycosylation.

Related Literature

Metal–organic framework-derived CuO catalysts for the efficient hydrogenolysis of hardwood lignin into phenolic monomers

Qian Xu, Qiang Wang, Ling-Ping Xiao, Xiao-Ying Li, Xi Xiao, Meng-Xin Li, Meng-Ran Lin, Yu-Man Zhao, Run-Cang Sun

2023-10-24 Paper

DOI: 10.1039/D3TA04927B

Back cover

2023-11-20 Cover

DOI: 10.1039/D3NH90058D

Looking back at 2023

2023-12-11 Editorial

DOI: 10.1039/D3NH90059B

Microfluidic synthesis of nanomaterials for biomedical applications

2023-09-05 Review Article

DOI: 10.1039/D3NH00217A

Albumin protein encapsulation into a ZIF-8 framework with Co-LDH-based hierarchical architectures for robust catalytic reduction

Maryam Chafiq, Abdelkarim Chaouiki, Tri Suhartono, Young Gun Ko

2023-10-30 Paper

DOI: 10.1039/D3TA03623E

Back cover

2023-11-21 Cover

DOI: 10.1039/D3TA90253F

siRNA-loaded DNA nanostructures restore endothelial leakiness

Arun Richard Chandrasekaran

2023-10-04 Editorial

DOI: 10.1039/D3NH90040A

Tumor microenvironment-responsive degradable silica nanoparticles: design principles and precision theranostic applications

Kaiyuan Tang, Zilu Liu, Zhijing Zhang, Shufan Duan, Hui Wang, Hui Yang, Dongliang Yang, Wenpei Fan

2023-11-29 Review Article

DOI: 10.1039/D3NH00388D

Defect engineering enhances plasmonic-hot electrons exploitation for CO2 reduction over polymeric catalysts

Zhehao Sun, Kaili Liu, Ary Anggara Wibowo, Julien Langley, Chao Zhang, Sandra E. Saji, Felipe Kremer, Dmitri Golberg, Hieu T. Nguyen, Nicholas Cox

2023-09-05 Communication

DOI: 10.1039/D3NH00348E

You might also like

Compound Q&A

What regulatory guidelines apply to 6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1)?

6-Bromo-2-methylimidazo[1,2-a]pyrimidine (CAS: 1111638-05-1) falls under various...

1111638-05-16-Bromo-2-methylimid...
Compound Q&A

Are there alternatives to 1-Pyrrolidineethanol, β-methyl-α-phenyl-, (αS,βR) (CAS: 123620-80-4) in synthesis?

While there are no direct alternatives, similar compounds like 1-Pyrrolidineetha...

123620-80-41-Pyrrolidineethanol...
Compound Q&A

Is 4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) safe?

4-Methyl-2,6-bis(2-methyl-2-propanyl)phenyl methylcarbamate (CAS: 1918-11-2) is ...

1918-11-24-Methyl-2,6-bis(2-m...
Compound Q&A

How should 2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) be stored?

2-(3-Bromo-4-fluorophenyl)-1,3-dioxolane (CAS: 77771-04-1) should be stored in a...

77771-04-12-(3-Bromo-4-fluorop...
Compound Q&A

What are the physical and chemical properties of 4,5,6,7-Tetrahydro-1H-indazole hydrochloride (CAS: 18161-11-0)?

4,5,6,7-Tetrahydro-1H-indazole hydrochloride is a white crystalline solid with a...

18161-11-04,5,6,7-Tetrahydro-1...
Compound Q&A

What is (2R)-1-Methoxy-3-phenyl-2-propanamine (CAS: 59919-07-2)?

(2R)-1-Methoxy-3-phenyl-2-propanamine is a chiral organic compound with the CAS ...

59919-07-2(2R)-1-Methoxy-3-phe...
Compound Q&A

What industries use Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate (CAS: 56649-47-9)?

Ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate is used in various industries...

56649-47-9Ethyl 1-(1-phenyleth...
Compound Q&A

What regulatory guidelines apply to 4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3)?

4-[(1E,3S)-1-(4-Hydroxyphenyl)-1,4-pentadien-3-yl]phenol (CAS: 17676-24-3) falls...

17676-24-34-[(1E,3S)-1-(4-Hydr...
Compound Q&A

What industries use (S)-3-Amino-5-phenylpentanoic acid hydrochloride (CAS: 331846-97-0)?

(S)-3-Amino-5-phenylpentanoic acid hydrochloride is primarily used in the pharma...

331846-97-0(S)-3-Amino-5-phenyl...
Compound Q&A

How is 7-methoxy-1-benzothiophene-2-carboxylic acid (CAS: 88791-07-5) typically synthesized?

7-Methoxy-1-benzothiophene-2-carboxylic acid is typically synthesized by reactin...

88791-07-57-methoxy-1-benzothi...

Source Journal

Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
CiteScore: 3.4
Self-citation Rate: 10.3%
Articles per Year: 1041

Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.