Protecting groups

Jarowicki, Krzysztof; Kocieński, Philip

doi:10.1039/b103282h

Cited by 98 publications

(41 citation statements)

References 95 publications

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“…The benzylidene acetal can also be regioselectively opened under reductive conditions to produce partially benzylated derivatives [12–14]. A number of methods have been reported for the removal of benzylidene acetals by using strong protic and Lewis acids [10–11 15] as well as some heterogeneous acidic catalysts [16–17]. Removal of benzylidene acetal under nonacidic conditions includes hydrogenolysis using hydrogen gas over Pd/C [18], or treatment with hydrazine [19] or EtSH [20] or Na/NH 3 [21], etc.…”

Section: Introductionmentioning

confidence: 99%

Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C

Santra¹,

Ghosh

Misra³

2013

Beilstein J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C

Santra¹,

Ghosh

Misra³

2013

Beilstein J. Org. Chem.

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“…The DMTr protecting group was incorporated and the conversion of the secondary alcohol 10 to phosphoramidite 11 was performed. The base-labile cyanoethyl group [51–52] is known to be resistant under synthesis conditions for the preparation of the phosphoramidite building block and for solid-phase oligonucleotide synthesis [49,53]. …”

Section: Resultsmentioning

confidence: 99%

DNA functionalization by dynamic chemistry

Kanlidere¹,

Jochim²,

Cal³

et al. 2016

Beilstein J. Org. Chem.

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SummaryDynamic combinatorial chemistry (DCC) is an attractive method to efficiently generate libraries of molecules from simpler building blocks by reversible reactions under thermodynamic control. Here we focus on the chemical modification of DNA oligonucleotides with acyclic diol linkers and demonstrate their potential for the deoxyribonucleic acid functionalization and generation of libraries of reversibly interconverting building blocks. The syntheses of phosphoramidite building blocks derived from D-threoninol are presented in two variants with protected amino or thiol groups. The threoninol building blocks were successfully incorporated via automated solid-phase synthesis into 13mer oligonucleotides. The amino group containing phosphoramidite was used together with complementary single-strand DNA templates that influenced the Watson–Crick base-pairing equilibrium in the mixture with a set of aldehyde modified nucleobases. A significant fraction of all possible base-pair mismatches was obtained, whereas, the highest selectivity (over 80%) was found for the guanine aldehyde templated by the complementary cytosine containing DNA. The elevated occurrence of mismatches can be explained by increased backbone plasticity derived from the linear threoninol building block as a cyclic deoxyribose analogue.

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“…The use of a silyl ether function as a protecting group of the hydroxy functionality is well documented in organic synthesis. 2 Several methods have become available for silylation of hydroxy functional groups using a variety of silylating agents, such as trimethylsilyl chloride in the presence of a base, 3 Li 2 S, 4 or Mg, 5 ketene methyltrialkylsilyl acetals, 6 allyl silanes, 7 ethyl trimethylsilyl acetate, 8 N, (p-TsCl)-Catalyzed Trimethylsilylation N-bis(trimethylsilylurea), 9 methyl 3-(trimethylsilyloxy)crotonate, 10 trimethylsilyl azide, 11 N-trimethylsilyl-2-oxazolidinone, 12 N, Obis(trimethylsilyl)acetamide, 13 and hexamethyldisilane. 14 However, some of these silylating agents suffer from drawbacks such as lack of reactivity or difficulty in removal of byproducts of the silylation reaction.…”

Section: Introductionmentioning

confidence: 97%