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Literature DB >> 19115840

Practical synthesis of 3beta-amino-5-cholestene and related 3beta-halides involving i-steroid and retro-i-steroid rearrangements.

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.

Entities: Chemical Disease Gene Species

Mesh：

Substances：

Year: 2009 PMID： 19115840 PMCID： PMC2651230 DOI： 10.1021/ol802343z

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

14 in total

1. Endocytic delivery of vancomycin mediated by a synthetic cell surface receptor: rescue of bacterially infected Mammalian cells and tissue targeting in vivo.

Authors: Siwarutt Boonyarattanakalin; Jianfang Hu; Sheryl A Dykstra-Rummel; Avery August; Blake R Peterson
Journal: J Am Chem Soc Date: 2007-01-17 Impact factor: 15.419

Review 2. Synthetic mimics of mammalian cell surface receptors: prosthetic molecules that augment living cells.

Authors: Blake R Peterson
Journal: Org Biomol Chem Date: 2005-09-08 Impact factor: 3.876

Review 3. Low-density lipoprotein as a vehicle for targeting antitumor compounds to cancer cells.

Authors: R A Firestone
Journal: Bioconjug Chem Date: 1994 Mar-Apr Impact factor: 4.774

4. Studies on the origin of stereoselectivity in the synthesis of 1,2-trans glycofuranosyl azides.

Authors: A Stimac; J Kobe
Journal: Carbohydr Res Date: 2000-02-25 Impact factor: 2.104

5. Synthetic mimics of small Mammalian cell surface receptors.

Authors: Siwarutt Boonyarattanakalin; Scott E Martin; Sheryl A Dykstra; Blake R Peterson
Journal: J Am Chem Soc Date: 2004-12-22 Impact factor: 15.419

6. Squalamine: an aminosterol antibiotic from the shark.

Authors: K S Moore; S Wehrli; H Roder; M Rogers; J N Forrest; D McCrimmon; M Zasloff
Journal: Proc Natl Acad Sci U S A Date: 1993-02-15 Impact factor: 11.205

7. Benzophenone-containing cholesterol surrogates: synthesis and biological evaluation.

Authors: Thomas A Spencer; Pingzhen Wang; Dansu Li; Jonathon S Russel; David H Blank; Jarkko Huuskonen; Phoebe E Fielding; Christopher J Fielding
Journal: J Lipid Res Date: 2004-06-01 Impact factor: 5.922

8. Selective disruption of early/recycling endosomes: release of disulfide-linked cargo mediated by a N-alkyl-3beta-cholesterylamine-capped peptide.

Authors: Qi Sun; Sutang Cai; Blake R Peterson
Journal: J Am Chem Soc Date: 2008-07-10 Impact factor: 15.419

9. Rates of spontaneous exchange of synthetic radiolabeled sterols between lipid vesicles.

Authors: C C Kan; J Yan; R Bittman
Journal: Biochemistry Date: 1992-02-18 Impact factor: 3.162

10. Distribution and transport of cholesterol-rich membrane domains monitored by a membrane-impermeant fluorescent polyethylene glycol-derivatized cholesterol.

Authors: Satoshi B Sato; Kumiko Ishii; Asami Makino; Kazuhisa Iwabuchi; Akiko Yamaji-Hasegawa; Yukiko Senoh; Isao Nagaoka; Hitoshi Sakuraba; Toshihide Kobayashi
Journal: J Biol Chem Date: 2004-03-16 Impact factor: 5.157

8 in total

Practical synthesis of 3beta-amino-5-cholestene and related 3beta-halides involving i-steroid and retro-i-steroid rearrangements.

1. Endocytic delivery of vancomycin mediated by a synthetic cell surface receptor: rescue of bacterially infected Mammalian cells and tissue targeting in vivo.

Review 2. Synthetic mimics of mammalian cell surface receptors: prosthetic molecules that augment living cells.

Review 3. Low-density lipoprotein as a vehicle for targeting antitumor compounds to cancer cells.

4. Studies on the origin of stereoselectivity in the synthesis of 1,2-trans glycofuranosyl azides.

5. Synthetic mimics of small Mammalian cell surface receptors.

6. Squalamine: an aminosterol antibiotic from the shark.

7. Benzophenone-containing cholesterol surrogates: synthesis and biological evaluation.

8. Selective disruption of early/recycling endosomes: release of disulfide-linked cargo mediated by a N-alkyl-3beta-cholesterylamine-capped peptide.

9. Rates of spontaneous exchange of synthetic radiolabeled sterols between lipid vesicles.

10. Distribution and transport of cholesterol-rich membrane domains monitored by a membrane-impermeant fluorescent polyethylene glycol-derivatized cholesterol.

Review 1. Synthetic cell surface receptors for delivery of therapeutics and probes.

2. Interaction of 3β-amino-5-cholestene with phospholipids in binary and ternary bilayer membranes.

3. Rhenium(I) conjugates as tools for tracking cholesterol in cells.

4. Fluorescent mimics of cholesterol that rapidly bind surfaces of living mammalian cells.

5. Synthesis of cholesteryl-α-D-lactoside via generation and trapping of a stable β-lactosyl iodide.

6. Drug Delivery via Cell Membrane Fusion Using Lipopeptide Modified Liposomes.

7. Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners.

8. Membrane-Fusogen Distance Is Critical for Efficient Coiled-Coil-Peptide-Mediated Liposome Fusion.