Selective transformation of O-2-(trimethylsilyl)ethyl and O-tert-butyl carbamates into O-benzyl carbamates using benzyl trichloroacetimidate

Barrett, Anthony G. M.; Pilipauskas, Daniel

doi:10.1021/jo00304a035

Cited by 17 publications

(15 citation statements)

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“…Dipeptide amide starting materials 3a-i and reference compound 5 were synthesised by solution-phase peptide synthesis using the EDC/ HOAt strategy or by standard SPPS on a Rink-amide resin. Analytical data of compounds 2b, [15] 4a, [16] 4b, [17] 4 c, [18] 4e, [19] 6, [20] 11, [21] 12 [22] and 13 [23] were found identical to those reported in the literature. The identity of compounds 2a, 2c, 10 and 15 was ascertained by comparison with commercially available samples (Bachem, Switzerland).…”

Section: Methodssupporting

confidence: 81%

Fully Enzymatic N→C‐Directed Peptide Synthesis Using C‐Terminal Peptide α‐Carboxamide to Ester Interconversion

et al. 2011

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Chemoenzymatic peptide synthesis is potentially the most cost-efficient technology for the synthesis of short and medium-sized peptides with some important advantages. For instance, stoichiometric amounts of expensive coupling reagents are not required and racemisation does not occur rendering purification easier compared to chemical peptide synthesis. In this paper, a novel interconversion reaction of peptide C-terminal a-carboxamides into primary alkyl esters with alcalase was used to develop a fully enzymatic peptide synthesis strategy. For each elongation step a cost-efficient amino acid carboxamide building block was used followed by the interconversion of the elongated peptide carboxamide to the corresponding primary alkyl ester. These peptide esters are the starting materials for the next enzymatic peptide elongation step.

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Section: Methodssupporting

confidence: 81%

Fully Enzymatic N→C‐Directed Peptide Synthesis Using C‐Terminal Peptide α‐Carboxamide to Ester Interconversion

et al. 2011

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“…Infrared spectra were recorded on an IR Affinity-1. NMR spectra were measured in CDCl 3 (with TMS as internal standard) or D 2 O or MeOD on a Bruker AV400 ( 1 H at 400 MHz, 13 C at 100 MHz, 19 F at 376 MHz) magnetic resonance spectrometer. High-resolution mass spectra (HRMS) were recorded on a SYNAPT G2Si High Definition MS System.…”

Section: General Informationmentioning

confidence: 99%

“…General procedure for the synthesis of the substrates and 1 H NMR, 13 C NMR spectra of products. The Supporting Information is available free of charge via the Internet at http://sioc-journal.cn/.…”

Section: Supporting Informationmentioning

confidence: 99%

Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor

Zeng¹,

Duan²,

Zhao³

et al. 2018

Chin. J. Org. Chem.

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Selectfluor, 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo-[2.2.2] octane bis(tetrafluoroborate), is among the most popular fluorinating reagents owning to its commercially availability and non-hygroscopic property. The discovery and understanding of new reactivities of selectfluor are thus important for reaction design and optimization when this popular reagent is employed. It has been found that selectfluor could selectively remove Boc group from doubly protected amines in acetonitrile. This deprotection could be of interest when compared to other reported methods, not only because selectfluor is a solid and easy-to-handle, but also because the reaction is mild, operationally simple and chemoselective. The potential usefulness of this method is demonstrated by the deprotection of a series of protected amino acids and a one-step synthesis of pharmaceutically important purine derivative. The NMR experiments conducted in CD 3 CN explain why stoichiometric amount of selectfluor is needed for a successful reaction.

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“…[25] In an alternative approach, we envisaged that protection of the oxygen would be an advantage. The enantiomerically enriched mono-acetate 2 was benzylated using benzyl trichloroacetimidate, in the presence of a catalytic amount of triflic acid, [27] to afford the Nbenzyloxycarbonyl-O-benzyl acylated serinol 7 in reasonable yield. Cyclisation with potassium carbonate then provided the (R)-oxazolidinone 8 in >99% ee (Scheme 7).…”

Section: Preparation Of Enantiomerically Enriched 2-oxazolidinones Bymentioning

confidence: 99%

“…Enantiomeric excesses were calculated comparing the obtained specific rotations with that of the pure compound reported in literature {Lit. [27] [a] D 30 : 32.2 (c 1.04, MeOH)}.…”

Section: General Procedures For the Enzymatic Hydrolysis Of (R/s)-( / mentioning

confidence: 99%

New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies

Neri

Williams

2003

Adv Synth Catal

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This paper describes how enantiomerically enriched Evans auxiliaries can be successfully prepared by either an enzymatic desymmetrisation strategy or an asymmetric synthesis using racemic auxiliaries and an enzymatic resolution. Desymmetrisation of N-Boc-protected serinol has been achieved in good yield and high enantiomeric excess using porcine pancreas lipase. This has been exploited in different ways to prepare enantiomerically enriched (4R)-and (4S)-substituted 2-oxazolidinones. In another approach to asymmetric synthesis, starting from a racemic Evans auxiliary, by means of a diastereoselective aldol reaction coupled with a lipase-catalysed resolution, we achieved the preparation of enantiomerically enriched b-hydroxy acids and enantiomerically enriched 2-oxazolidinones.

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Selective transformation of O-2-(trimethylsilyl)ethyl and O-tert-butyl carbamates into O-benzyl carbamates using benzyl trichloroacetimidate

Cited by 17 publications

References 0 publications

Fully Enzymatic N→C‐Directed Peptide Synthesis Using C‐Terminal Peptide α‐Carboxamide to Ester Interconversion

Fully Enzymatic N→C‐Directed Peptide Synthesis Using C‐Terminal Peptide α‐Carboxamide to Ester Interconversion

Efficient and Chemoselective Deprotection of N-t-Butyloxycarbonyl Group Mediated by Selectfluor

New Routes to Chiral Evans Auxiliaries by Enzymatic Desymmetrisation and Resolution Strategies

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