Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide
Тип публикации: Journal Article
Дата публикации: 1988-01-01
scimago Q3
wos Q2
БС2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
A 7-step sequence is described for the controlled removal of D -desosamine and L -oleandrose from oleandomycin to give the C 3 ,C 5 -acetonide 2. A Cope elimination was first used to remove the NMe 2 group of desosamine, 3 → 4. Treatment of 4 with hydroiodic acid gave the iodohydrin 12 with loss of oleandrose, which was followed by removal of the olefinic sugar by hydrolysis with dilute hydrochloric acid to give 14. Acetonide formation and regeneration of the C 8 epoxide by mild base then gave 2. The conversion of the C 8 epoxide of 4 to the glycols 5 and 6, the enone 7, and the phenylsulphide 8 is also described.
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PATERSON I., Arya P. Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide // Tetrahedron. 1988. Vol. 44. No. 1. pp. 253-260.
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PATERSON I., Arya P. Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide // Tetrahedron. 1988. Vol. 44. No. 1. pp. 253-260.
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TY - JOUR
DO - 10.1016/s0040-4020(01)85115-2
UR - https://doi.org/10.1016/s0040-4020(01)85115-2
TI - Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide
T2 - Tetrahedron
AU - PATERSON, IAN
AU - Arya, Prabhat
PY - 1988
DA - 1988/01/01
PB - Elsevier
SP - 253-260
IS - 1
VL - 44
SN - 0040-4020
SN - 1464-5416
ER -
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@article{1988_PATERSON,
author = {IAN PATERSON and Prabhat Arya},
title = {Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide},
journal = {Tetrahedron},
year = {1988},
volume = {44},
publisher = {Elsevier},
month = {jan},
url = {https://doi.org/10.1016/s0040-4020(01)85115-2},
number = {1},
pages = {253--260},
doi = {10.1016/s0040-4020(01)85115-2}
}
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MLA
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PATERSON, IAN, and Prabhat Arya. “Degradation of oleandomycin: controlled removal of sugars to give oleandonolide c3,c5-acetonide.” Tetrahedron, vol. 44, no. 1, Jan. 1988, pp. 253-260. https://doi.org/10.1016/s0040-4020(01)85115-2.