Synthesis of Chiral Pilocarpine Analogues via a C-8 Ketone Intermediate

Holden, Kenneth G.; Mattson, Matthew N.; Hoi, Kyung; Rapoport, Henry

doi:10.1021/jo0111210

Cited by 30 publications

(18 citation statements)

References 13 publications

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“…Although it is described that Thp esters are easily hydrolyzed, some authors report that they are easily cleaved in mildly acidic conditions such as by treatment with a mixture of acetic acid/THF/H 2 O (4:2:1) at 45 °C . According to our results, complete removal of Thp from Fmoc‐Gly‐OThp requires the use of TFA at greater than 10 % concentration.…”

Section: Thp Protection Of the Carboxyl Groupsupporting

confidence: 57%

“…However, undesired removal of Thp from other amino acids was observed during aqueous work‐up. This could be attributed to the high lability of the hemiacetal esters, as previously described . Therefore, after monitoring the reaction to completion by using thin‐layer chromatography, N , N ‐diisopropylethylamine (DIEA) was added as a part of the work‐up to neutralize the PTSA used during the reaction.…”

Section: Thp Protection Of the Carboxyl Groupmentioning

confidence: 99%

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Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

et al. 2017

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Tetrahydropyranyl (Thp) is recognized as a useful protecting group for alcohols in organic synthesis. It has several advantages, including low cost, ease of introduction, general stability to most non‐acidic reagents, it confers good solubility, and the ease with which it can be removed if the functional group it protects requires manipulation. However, little attention has been paid to Thp in peptide chemistry. Provided here is a concise analysis of the Thp protection of various amino acid functionalities (OH, SH, NH and COOH) and its application to peptide synthesis. Thp is a useful moiety for the side‐chain protection of serine, threonine and cysteine and is suitable for the Fmoc/tBu solid‐phase peptide synthesis strategy. The immobilized version of 3,4‐dihydro‐2H‐pyran, the so‐called Ellman resin, is also discussed as a useful solid support for anchoring the side chains of serine, threonine and tryptophan residues.

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Section: Thp Protection Of the Carboxyl Groupsupporting

confidence: 57%

Section: Thp Protection Of the Carboxyl Groupmentioning

confidence: 99%

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

et al. 2017

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“…The generated imidazolylmagnesium halide has been employed in addition reactions to carbonyl compounds for the preparation, for example, of ligands for the a 2D adrenergic receptor [218], sugar-mimic glycosidase inhibitors [219] or C-nucleosides [220]. It has also been used in acylation reactions with esters in the synthesis of pilocarpine analogues [221] or with Weinreb amides such as 145 (Scheme 10.67) [222].…”

Section: Magnesium Azolesmentioning

confidence: 99%

Five‐Membered Heterocycles: 1,3‐Azoles

Revuelta¹,

Machetti²,

Cicchi³

2011

Modern Heterocyclic Chemistry

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“…This is done in the presence of the strong acid benzene sulfonic acid in CCl 4 . The final product is L-/D-serine benzyl ester benzene sulfonate (II) [9]. Due to the commercial availability of substance (II), synthesis of the diastereomeric salts started from it.…”

Section: L-/d-serine Benzyl Ester Benzene Sulfonatementioning

confidence: 99%

Application of Classical Resolution for Separation of DL‐Serine

et al. 2010

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For resolution of chiral compound-forming substances diastereomeric salt formation is the most important classical separation technique. Diastereomeric salts possess different physical and chemical properties, e.g., solubilities, which facilitate the effective separation via crystallization. A maximum recovery of both diastereomeric salts is usually unachievable when there is a lack of quantitative information regarding solubility and metastable zone width. The present work provides experimental results for the formation of diastereomeric salts of DL-serine. As basic thermodynamic data binary melting and ternary solubility phase diagrams are shown and discussed. A plan for a series of crystallization processes is suggested for the recovery of both salts in pure form with a maximum possible yield. Copyright © 1999-2010 John Wiley & Sons, Inc. All Rights Reserved. [accessed May 7, 2010

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Synthesis of Chiral Pilocarpine Analogues via a C-8 Ketone Intermediate

Cited by 30 publications

References 13 publications

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

Understanding Tetrahydropyranyl as a Protecting Group in Peptide Chemistry

Five‐Membered Heterocycles: 1,3‐Azoles

Application of Classical Resolution for Separation of DL‐Serine

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