Nucleic acid related compounds. 30. Transformations of adenosine to the first 2',3'-aziridine-fused nucleosides, 9-(2,3-epimino-2,3-dideoxy-.beta.-D-ribofuranosyl)adenine and 9-(2,3-epimino-2,3-dideoxy-.beta.-D-lyxofuranosyl)adenine

Robins, Morris J.; Hawrelak, S. D.; Kanai, Tadashi; SIEFERT, J. M.; Mengel, Rudolf

doi:10.1021/jo01322a026

Cited by 49 publications

(17 citation statements)

References 3 publications

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“…Subsequent selective removal of the C-1 protecting group and oxidation should yield the desired aldehyde 19. Therefore, hemiacetal3 was reduced with sodium borohydride (31) to furnish the trio1 22, which was selectively protected at C-1 by treatment with pivaloyl chloride (32), giving the pivaloate ester 23 in good yield. Benzylation of the free hydroxyl groups yielded the tribenzyl ether 24, which was then treated with sodium methoxide in methanol to remove the pivaloate ester at C-1 and expose the primary alcohol (25).…”

Section: Resultsmentioning

confidence: 99%

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

Bird¹,

Dolphin²,

Withers³

1990

Can. J. Chem.

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The successful syntheses of 5-azido-2,3,4,6-tetra-O-benzyl-5-deoxy-~-glucononitrile and 2,3,4,6-tetra-0-benzyl-5-deoxy-5-trifluoroacetarnido-D-glucononitrile starting from D-glucose are described. Unsuccessful attempts were made to convert these two compounds into a protected 5-amino-5-deoxy-D-glucononitrile and to subsequently cyclize them to an amidine analogue of glucose as a possible glycosidase inhibitor. On dCcrit des synthkses rCalisables des 5-azido-2,3,4,6-tCtra-0-benzyl-5-dCsoxy-et 2,3,4,6-tttra-0-benzyl-5-dCsoxy-5-trifluoroacCtamido-D-glucononitriles ?I partir du D-glucose. On a essay6 sans succks de transformer ces deux compos6s en un ~-amino-5-d6soxy-~-glucononitrile et Cventuellement de les cycliser en une amidine analogue du glucose qui aurait pu &tre tvaluCe cornrne inhibiteur de la glycosidase.Mots cle's : synthkse, amino-sucres, inhibiteurs de la glycosidase.[Traduit par la revue]

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Section: Resultsmentioning

confidence: 99%

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

Bird¹,

Dolphin²,

Withers³

1990

Can. J. Chem.

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“…Hydroxyl groups are very reactive toward many reagents and can be readily protected by formation of an ether, a silyl ether, or an ester . In this work, by taking advantage of the reactive OH group located at each P γ BL chain end, we first utilized the above reactions to convert P γ BL‐OH chains into P γ BL‐OR by end‐capping with reactive acyl chloride, silyl chloride, or anhydride reagents.…”

Section: Introductionmentioning

confidence: 99%

Effects of Chain Ends on Thermal and Mechanical Properties and Recyclability of Poly(γ‐butyrolactone)

Tang

Chen

2018

J. Polym. Sci. Part A: Polym. Chem.

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This work investigates effects of poly(γ‐butyrolactone) (PγBL) with different initiation and termination chain ends on five types of materials properties, including thermal stability, thermal transitions, thermal recyclability, hydrolytic degradation, and dynamic mechanical behavior. Four different chain‐end‐capped polymers with similar molecular weights, BnO‐[C(=O)(CH2)3O]n‐R, R = C(=O)Me, C(=O)CH=CH2, C(=O)Ph, and SiMe2CMe3, along with a series of uncapped polymers R′O‐[C(=O)(CH2)3O]n‐H (R′ = Bn, Ph2CHCH2) with Mn ranging from low (4.95 kg mol−1) to high (83.2 kg mol−1), have been synthesized. The termination chain end R showed a large effect on polymer decomposition temperature and hydrolytic degradation, relative to H. Overall, for those properties sensitive to the chain ends, chain‐end capping renders R‐protected linear PγBL behaving much like cyclic PγBL. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2271–2279

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“…Subsequent treatment of 13 with DIBAL-H in CH 2 Cl 2 at -78 °C for 1h afforded the allyl alcohol whose primary hydroxyl was protected as the MEM-ether (14). 13 The structural identity was secured by the interpretation of the 1 H NMR spectrum.…”

Section: 12mentioning

confidence: 98%

“…14 was hydrogenolysed in the presence of Pd/C and consequently exposed to LAH in THF to produce the diol derivative (16). In order to introduce iodide at C-1, the protection-deprotection [14][15][16] sequence on 16 was performed to obtain the primary hydroxyl derivative (17). Treatment of 17 with I 2 , TPP and imidazole in toluene at room temperature led to the formation of 7 in 40% yield.…”

Section: 12mentioning

confidence: 99%

Ring-closing metathesis mediated total synthesis of microcarpalide and herbarumin III

Gurjar¹,

Nagaprasad²,

Ramana³

et al. 2005

Arkivoc

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Nucleic acid related compounds. 30. Transformations of adenosine to the first 2',3'-aziridine-fused nucleosides, 9-(2,3-epimino-2,3-dideoxy-.beta.-D-ribofuranosyl)adenine and 9-(2,3-epimino-2,3-dideoxy-.beta.-D-lyxofuranosyl)adenine

Cited by 49 publications

References 3 publications

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

The synthesis of protected 5-azido-5-deoxy-D-glucononitriles as precursors of glycosidase inhibitors

Effects of Chain Ends on Thermal and Mechanical Properties and Recyclability of Poly(γ‐butyrolactone)

Ring-closing metathesis mediated total synthesis of microcarpalide and herbarumin III

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