ArticleOrganic letters2009
Practical synthesis of 3beta-amino-5-cholestene and related 3beta-halides involving i-steroid and retro-i-steroid rearrangements.
Article in Organic letters, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed, 52 citations in OpenAlex.
- Revisiting the bromination of 3β-hydroxycholest-5-ene with CBrBeilstein journal of organic chemistry · 2023Article
- Rhenium(I) conjugates as tools for tracking cholesterol in cells.Metallomics : integrated biometal science · 2022Article
- Membrane-Fusogen Distance Is Critical for Efficient Coiled-Coil-Peptide-Mediated Liposome Fusion.Langmuir : the ACS journal of surfaces and colloids · 2017Article
- Drug Delivery via Cell Membrane Fusion Using Lipopeptide Modified Liposomes.ACS central science · 2016Article
- Fluorescent mimics of cholesterol that rapidly bind surfaces of living mammalian cells.Chemical communications (Cambridge, England) · 2015Article
- Synthesis of cholesteryl-α-D-lactoside via generation and trapping of a stable β-lactosyl iodide.Tetrahedron letters · 2015Article
- Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners.Beilstein journal of organic chemistry · 2015Article
- Synthetic cell surface receptors for delivery of therapeutics and probes.Advanced drug delivery reviews · 2012Review
- Interaction of 3β-amino-5-cholestene with phospholipids in binary and ternary bilayer membranes.Langmuir : the ACS journal of surfaces and colloids · 2012Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Derivatives of 3beta-amino-5-cholestene (3beta-cholesterylamine) are of substantial interest as cellular probes and have potential medicinal applications. However, existing syntheses of 3beta-amino-5-cholestene are of limited preparative utility. We report here a practical method for the stereoselective preparation of 3beta-amino-5-cholestene, 3beta-chloro-5-cholestene, 3beta-bromo-5-cholestene, and 3beta-iodo-5-cholestene from inexpensive cholesterol. A sequential i-steroid/retro-i-steroid rearrangement promoted by boron trifluoride etherate and trimethylsilyl azide converted cholest-5-en-3beta-ol methanesulfonate to 3beta-azido-cholest-5-ene with retention of configuration in 93% yield.
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What OpenQuestion holds
Registered trials
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.