Use of the 3,5-Dimethoxybenzyloxycarbonyl Group as a Photosensitive N-Protecting Group

Chamberlin, James W.

doi:10.1021/jo01343a516

Cited by 71 publications

(26 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Photolabile protection of amino acids and dipeptides was further demonstrated by Chamberlin, who used the 3,5-dimethoxybenzyloxycarbonyl protecting group ( 166 ). 311 Substrates were released in up to 85% yield upon illumination with a high-pressure mercury lamp for 1.5 h.…”

Section: Arylmethyl Groupsmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

View full text Add to dashboard Cite

Section: Arylmethyl Groupsmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

View full text Add to dashboard Cite

“…[48] Derivatives of the 3,5-dimethoxybenzyl alcohol protecting group can be removed with higher energy light (< 300 nm) and were shown to be inert above 350 nm, which suggests that it can be used in combination with the 2-nitroveratryl system for orthogonal protection. [49] Blanc and Bochet have shown that by carefully choosing two different carboxylic acid protecting groups, either could be selectively removed from the differentially protected diacid 73 with a particular wavelength of incident light.…”

Section: Electron Transfer: Electrosynthesis and Photochemistrymentioning

confidence: 99%

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

2009

View full text Add to dashboard Cite

Achieving high levels of chemoselectivity has been the Achilles' heel of chemical synthesis. The excitement generated by the successful realization of chemoselective strategies underscores the painstaking efforts to define a set of conditions conducive to selection among the available reaction pathways. We discuss in this Review various aspects of chemoselectivity that have been addressed in a range of synthetic methods over the past decade. We have focused on the proposed mechanistic basis of the reactions under consideration in an attempt to categorize them and highlight the key concepts that have been emerging on the basis of these studies. Our overview of recent advances in chemoselective processes suggests that significant progress has been made, but a lot of challenges lie ahead.

show abstract

“…Compounds 13, 14, and 15 were prepared from the corresponding 4-substituted benzyloxycarbonyl-L-proline derivatives (Tm oil, 138.5-140.5°C and 90-93.5°C, respectively) which were in turn prepared from the corresponding benzyl alcohols by the nitrophenyl carbonate procedure of Chamberlin (2).…”

Section: Methodsmentioning

confidence: 99%

Peptide Alcohols as Promoters of Nitrate and Ammonium Ion Uptake in Plants

Lin¹,

Kauer²

1985

Plant Physiol.

View full text Add to dashboard Cite

Several aryl-carbamoyl dipeptide alcohols increased the uptake of nitrate and ammonium ions into corn root segments by up to 50% and 90%, respectively. The most effective one was N-carbobenzoxy-L-prolyl-L-valinol. Foliar application of this compound to underfertilized corn plants caused an increase in the rate of plant growth in the greenhouse and provided modest (6-10%) corn yield increases in field tests in Delaware.

show abstract

Use of the 3,5-Dimethoxybenzyloxycarbonyl Group as a Photosensitive N-Protecting Group

Cited by 71 publications

References 2 publications

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

Peptide Alcohols as Promoters of Nitrate and Ammonium Ion Uptake in Plants

Contact Info

Product

Resources

About