Evidence map›Paper›PMID 19243158›Full record

ArticleThe Journal of organic chemistry2009

The 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group: a new alcohol protecting group, fully orthogonal with the p-methoxybenzyl group and removable under desilylation conditions.

David Crich, Linfeng Li, Michio Shirai

Open access · greenAbstract read
In one paragraph

Article in The Journal of organic chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
0.8field-weighted citation impact, top 27% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed, 15 citations in OpenAlex.

  1. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

3 authors at 2 institutions in 3 countries.

David CrichDepartment of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA. dcrich@icsn.cnrs-gif.fr
Linfeng Li
Michio Shirai
Institut de Chimie des Substances Naturelles · FRUniversity of Illinois Chicago · US

Funding

Methods and Mechanisms in Carbohydrate ChemistryR01GM062160 · NIGMS · WAYNE STATE UNIVERSITY · PI CRICH, DAVID · 2001 to 2024
$7.1M
CHEMICAL SYNTHESIS OF BETA MANNO- AND RHAMNOPYRANOSIDESR01GM057335 · NIGMS · WAYNE STATE UNIVERSITY · PI CHA, JIN K · 1998 to 2009
$2.7M
NIGMS NIH HHS GM57335NIGMS NIH HHS GM62160NIGMS NIH HHS R01 GM057335NIGMS NIH HHS R01 GM062160
6 · The paper itself

Abstract

A new benzyl ether-type protecting group for alcohols, the 4-(tert-butyldiphenylsiloxy)-3-fluorobenzyl group, is introduced. The protecting group is introduced by means of the readily prepared benzyl bromide and is cleaved with tetrabutylammonium fluoride in dimethylformamide under microwave irradiation. The fluoride substituent provides stability to oxidizing conditions, such that the new protecting group is fully compatible with the removal of p-methoxybenzyl ethers with DDQ. Applications of the new protecting group in the direct stereocontrolled synthesis of beta-mannopyranosides are presented.

Indexed as

AlcoholsBenzyl CompoundsMannoseMethodsMicrowavesQuaternary Ammonium CompoundsAlcoholsbenzyl bromideBenzyl CompoundsMannoseQuaternary Ammonium Compoundstetrabutylammonium

Identifiers

PMID19243158
PMCPMC3102264
OpenAlexW2058601895

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.