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Efficient stereoselective synthesis of α-C-glycopyranosides using 2,2′-azobis(2,4-dimethyl-4-methoxyvaleronitrile) [V-70]

✍ Scribed by Kentoku Gotanda; Masato Matsugi; Miki Suemura; Chiyo Ohira; Atsunori Sano; Masahisa Oka; Yasuyuki Kita


Book ID
104209555
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
624 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis


Abslma: Efticient synthesis of a-C-glycopyranosides through a radical addition reaction using 2.2'~axobis(2,4dimethy@methoxyvaleronitrile) [V-70] as an initiator under mild condition was developed. This method made it possible to completely control the stereocenter at the anomeric position and obtain only the aanomer in high yield compared with AJBN, EtJB, and photo irradiation methods.


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ChemInform Abstract: A Highly Stereosele
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A Highly Stereoselective Synthesis of α-Linked C-Glycopyranosides Using 2,2'-Azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70). -By using V-70 as an effective radical initiator at low temperature, a highly α-selective synthesis of C-glycopyranosides (III) is realized. -(KITA, Y.;

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The attributes of 2,2'-azobis-(2,4-dimethyl-4-methoxyvaleronitrile) (V-70), which is an effective radical initiator at low temperature, in contrast to 2,2'-azobisisobutyronitrile (AIBN) are described.