Optimisation of conditions for O-benzyl and N-benzyloxycarbonyl protecting group removal using an automated flow hydrogenator

被引：45

作者：

Knudsen, Kristian Rahbek

Holden, John

Ley, Steven V.

Ladlow, Mark

机构：

[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England

[2] Aitken Sci Ltd, Thame OX9 2AH, England

[3] Univ Cambridge, GlaxoSmithKline Cambridge Technol Ctr, Cambridge CB2 1EW, England

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 4-5期

关键词：

automation; debenzylation; deprotection; flow hydrogenation; palladium; peptides;

D O I：

10.1002/adsc.200600558

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A versatile, fully automated flow hydrogenator has been developed that is able to perform sequential flow optimisation experiments, flow library hydrogenation, or iterative scale-up hydrogenation. ne behaviour of a palladium catalyst in effecting removal of O-benzyl and N-benzyloxycarbonyl protecting groups has been investigated. Significant observations relating to maintaining optimal throughput are reported. A small library of peptidic derivatives has been deprotected in high yield and purity.

引用

收藏

页码：535 / 538

页数：4

相关论文

共 38 条

[1] Practical use of continuous processing in developing and scaling up laboratory processes [J].

Anderson, NG .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2001, 5 (06) :613-621

[2] Fully automated continuous flow synthesis of 4,5-disubstituted oxazoles [J].

Baumann, Marcus ;

Baxendale, Ian R. ;

Ley, Steven V. ;

Smith, Christoper D. ;

Tranmer, Geoffrey K. .

ORGANIC LETTERS, 2006, 8 (23) :5231-5234

[3] A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols [J].

Baxendale, Ian R. ;

Ley, Steven V. ;

Smith, Christopher D. ;

Tranmer, Geoffrey K. .

CHEMICAL COMMUNICATIONS, 2006, (46) :4835-4837

[4] Microwave-assisted Suzuki coupling reactions with an encapsulated palladium catalyst for batch and continuous-flow transformations [J].

Baxendale, Ian R. ;

Griffiths-Jones, Charlotte M. ;

Ley, Steven V. ;

Tranmer, Geoffrey K. .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (16) :4407-4416

[5] A flow process for the multi-step synthesis of the alkaloid natural product oxomaritidine: a new paradigm for molecular assembly [J].

Baxendale, Ian R. ;

Deeley, Jon ;

Griffiths-Jones, Charlotte M. ;

Ley, Steven V. ;

Saaby, Steen ;

Tranmer, Geoffrey K. .

CHEMICAL COMMUNICATIONS, 2006, (24) :2566-2568

[6] Preparation of the neolignan natural product grossamide by a continuous-flow process [J].

Baxendale, IR ;

Griffiths-Jones, CM ;

Ley, SV ;

Tranmer, GK .

SYNLETT, 2006, (03) :427-430

[7]

BAXENDALE IR, 2006, UNPUB CHEMMEDCHEM

[8]

Bonfils F, 2006, ORG BIOMOL CHEM, V4, P493, DOI 10.1039/b515241k

[9] On-microchip multiphase chemistry - a review of microreactor design principles and reagent contacting modes [J].

Doku, GN ;

Verboom, W ;

Reinhoudt, DN ;

van den Berg, A .

TETRAHEDRON, 2005, 61 (11) :2733-2742

[10]

Ehrfeld W., 2000, Microreactors: new technology for modern chemistry, DOI DOI 10.1002/3527601953

← 1 2 3 4 →