A Study on Synthesis and Upscaling of 2′-O-AECM-5-methyl Pyrimidine Phosphoramidites for Oligonucleotide Synthesis

2′-O-(N-(Aminoethyl)carbamoyl)methyl-modified 5-methyluridine (AECM-MeU) and 5-methylcytidine (AECM-MeC) phosphoramidites are reported for the first time and prepared in multigram quantities. The syntheses of AECM-MeU and AECM-MeC nucleosides are designed for larger scales (approx. 20 g up until phosphoramidite preparation steps) using low-cost reagents and minimizing chromatographic purifications. Several steps were screened for best conditions, focusing on the most crucial steps such as N3 and/or 2′-OH alkylations, which were improved for larger scale synthesis using phase transfer catalysis (PTC). Moreover, the need of chromatographic purifications was substantially reduced by employing one-pot synthesis and improved work-up strategies.

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Corrigendum to “One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction”

Tetrahedron Letters ◽

10.1016/j.tetlet.2005.07.003 ◽

2005 ◽

Vol 46 (36) ◽

pp. 6171 ◽

Cited By ~ 1

Author(s):

Shigeru Arai ◽

Kazuya Hasegawa ◽

Atsushi Nishida

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

Aldol Reaction ◽

One Pot ◽

Asymmetric Aldol ◽

One Pot Synthesis ◽

Asymmetric Aldol Reaction ◽

Catalytic Asymmetric

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ChemInform Abstract: Applications of Phase-Transfer Catalysis. Part 44. A One-Pot Synthesis of Trimethylsilyl Fluoride.

ChemInform ◽

10.1002/chin.198926221 ◽

1989 ◽

Vol 20 (26) ◽

Author(s):

E. V. DEHMLOW ◽

U. FASTABEND ◽

M. KESSLER

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

One Pot ◽

One Pot Synthesis

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ChemInform Abstract: A One-Pot Synthesis of Metol Sulfate Employing Phase-Transfer Catalysis.

ChemInform ◽

10.1002/chin.198930131 ◽

1989 ◽

Vol 20 (30) ◽

Author(s):

A. NAG ◽

S. K. SARKAR ◽

S. K. PALIT ◽

S. PANDEY

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

One Pot ◽

One Pot Synthesis

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One-Pot Synthesis of α-Diazo-β-hydroxyesters under Phase-Transfer Catalysis and Application to the Catalytic Asymmetric Aldol Reaction.

ChemInform ◽

10.1002/chin.200419050 ◽

2004 ◽

Vol 35 (19) ◽

Author(s):

Shigeru Arai ◽

Kazuya Hasegawa ◽

Atsushi Nishida

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

Aldol Reaction ◽

One Pot ◽

Asymmetric Aldol ◽

One Pot Synthesis ◽

Asymmetric Aldol Reaction ◽

Catalytic Asymmetric

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A Novel One-Pot Synthesis of Polyfunctionally Substituted Thiopyrano(2,3- b )pyridine and Pyrido(2,3- b )pyridine Derivatives under Solid-Liquid Phase-Transfer Catalysis

Phosphorus Sulfur and Silicon and the Related Elements ◽

10.1080/10426500211711 ◽

2002 ◽

Vol 177 (5) ◽

pp. 1213-1221 ◽

Cited By ~ 9

Author(s):

Ahmed M. M. El-Saghier

Keyword(s):

Liquid Phase ◽

Phase Transfer Catalysis ◽

Phase Transfer ◽

Pyridine Derivatives ◽

One Pot ◽

One Pot Synthesis ◽

Solid Liquid

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ChemInform Abstract: A “One Pot” Synthesis of 2-Aryl-4H-1-benzopyran-4-ones under Coupled Microwave Phase Transfer Catalysis (PTC) and Ultrasonic Irradiation PTC.

ChemInform ◽

10.1002/chin.200829134 ◽

2008 ◽

Vol 39 (29) ◽

Author(s):

Vijai N. Pathak ◽

Ragini Gupta ◽

Bindu Varshney

Keyword(s):

Ultrasonic Irradiation ◽

Phase Transfer Catalysis ◽

Phase Transfer ◽

One Pot ◽

One Pot Synthesis

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One-pot synthesis of α-diazo-β-hydroxyesters under phase-transfer catalysis and application to the catalytic asymmetric aldol reaction

Tetrahedron Letters ◽

10.1016/j.tetlet.2003.11.083 ◽

2004 ◽

Vol 45 (5) ◽

pp. 1023-1026 ◽

Cited By ~ 30

Author(s):

Shigeru Arai ◽

Kazuya Hasegawa ◽

Atsushi Nishida

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

Aldol Reaction ◽

One Pot ◽

Asymmetric Aldol ◽

One Pot Synthesis ◽

Asymmetric Aldol Reaction ◽

Catalytic Asymmetric

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ChemInform Abstract: Facile One-Pot Synthesis of 2,1,3-Benzoxadiazole N-Oxide (Benzofuroxan) Derivatives Under Phase-Transfer Catalysis.

ChemInform ◽

10.1002/chin.198750216 ◽

1987 ◽

Vol 18 (50) ◽

Author(s):

N. R. AYYANGAR ◽

S. M. KUMAR ◽

K. V. SRINIVASAN

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

One Pot ◽

One Pot Synthesis

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ONE—POT SYNTHESIS OF PYRIDINES, THIENOPYRIDINES, PYRROLOTHIENOPYRIDINES AND (1,8) NAPHTHYRIDINES UNDER PHASE-TRANSFER CATALYSIS CONDITIONS

Phosphorus Sulfur and Silicon and the Related Elements ◽

10.1080/10426500008046608 ◽

2000 ◽

Vol 163 (1) ◽

pp. 29-40 ◽

Cited By ~ 9

Author(s):

A. M. El-Sayed

Keyword(s):

Phase Transfer Catalysis ◽

Phase Transfer ◽

One Pot ◽

One Pot Synthesis

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Facile one-pot fabrication of a silica gel-supported chiral phase-transfer catalyst—N-(2-cyanobenzyl)-O(9)-allyl-cinchonidinium salt

Catalysis Science & Technology ◽

10.1039/c4cy01518e ◽

2015 ◽

Vol 5 (4) ◽

pp. 2141-2148 ◽

Cited By ~ 9

Author(s):

Dandan Feng ◽

Jinghan Xu ◽

Jingwei Wan ◽

Bing Xie ◽

Xuebing Ma

Keyword(s):

Silica Gel ◽

Phase Transfer ◽

Catalytic Performance ◽

Significant Loss ◽

Cinchona Alkaloid ◽

Phase Transfer Catalyst ◽

One Pot ◽

Chiral Phase ◽

One Pot Synthesis ◽

First Time

A novel silica gel-supported cinchona alkaloid-based PTC catalyst was prepared by one-pot synthesis for the first time. Excellent enantioselectivities (72.0–96.9% ee) and 80–96% yields in enantioselective α-alkylation were achieved without significant loss in the catalytic performance for five runs.

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