Syntheses of N4,2',3',5'-Tetraacylcytidines from N4-Acylcytosines, via Condensation with Tetraacylribose and Transribosylation with Acylated Purine Nucleosides

Yoshihiro Sugiura; S. Yuichi Furuya; Yoshiyasu Furukawa

doi:10.1248/cpb.36.3253

Syntheses of N⁴,2',3',5'-Tetraacylcytidines from N⁴-Acylcytosines, via Condensation with Tetraacylribose and Transribosylation with Acylated Purine Nucleosides

Yoshihiro Sugiura, S. Yuichi Furuya, Yoshiyasu Furukawa

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

N⁴-Isobutyryl- and -(2-ethylhexanoyl)cytosines (la, b) were synthesized by acylation of cytosine. Y⁴,2',3',5'-Tetraacylcytidines (III) were synthesized by two methods involving stannic chloride catalysis. One involves condensation of N⁴-acylcytosines (I) and l-0-acetyl-2,3,5-tri-0-benzoyl-β-D-ribofuranose (II), and the other involves transribosylation between N⁴-acylcytosines and acyl-inosines or -guanosines (IVa—d). N⁴-Octanoyl-2',3',5'-triacetylcytidine (Illf) was converted into cytidine by deacylation in a good yield.

Original language	English
Pages (from-to)	3253-3256
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	36
Issue number	9
DOIs	https://doi.org/10.1248/cpb.36.3253
Publication status	Published - 1988
Externally published	Yes

Keywords

2',3 ',5 ',-tetraacylcytidine
N4-acylcytosine N4
acylinosine
condensation acylribose
stannic chloride
synthesis acylguanosine
transribosylation

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

Access to Document

10.1248/cpb.36.3253

Cite this

@article{81cbafe598794bcaba8f1f8cd5b00cca,

title = "Syntheses of N4,2',3',5'-Tetraacylcytidines from N4-Acylcytosines, via Condensation with Tetraacylribose and Transribosylation with Acylated Purine Nucleosides",

abstract = "N4-Isobutyryl- and -(2-ethylhexanoyl)cytosines (la, b) were synthesized by acylation of cytosine. Y4,2',3',5'-Tetraacylcytidines (III) were synthesized by two methods involving stannic chloride catalysis. One involves condensation of N4-acylcytosines (I) and l-0-acetyl-2,3,5-tri-0-benzoyl-β-D-ribofuranose (II), and the other involves transribosylation between N4-acylcytosines and acyl-inosines or -guanosines (IVa—d). N4-Octanoyl-2',3',5'-triacetylcytidine (Illf) was converted into cytidine by deacylation in a good yield.",

keywords = "2',3 ',5 ',-tetraacylcytidine, N4-acylcytosine N4, acylinosine, condensation acylribose, stannic chloride, synthesis acylguanosine, transribosylation",

author = "Yoshihiro Sugiura and Furuya, {S. Yuichi} and Yoshiyasu Furukawa",

year = "1988",

doi = "10.1248/cpb.36.3253",

language = "English",

volume = "36",

pages = "3253--3256",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "9",

}

TY - JOUR

T1 - Syntheses of N4,2',3',5'-Tetraacylcytidines from N4-Acylcytosines, via Condensation with Tetraacylribose and Transribosylation with Acylated Purine Nucleosides

AU - Sugiura, Yoshihiro

AU - Furuya, S. Yuichi

AU - Furukawa, Yoshiyasu

PY - 1988

Y1 - 1988

N2 - N4-Isobutyryl- and -(2-ethylhexanoyl)cytosines (la, b) were synthesized by acylation of cytosine. Y4,2',3',5'-Tetraacylcytidines (III) were synthesized by two methods involving stannic chloride catalysis. One involves condensation of N4-acylcytosines (I) and l-0-acetyl-2,3,5-tri-0-benzoyl-β-D-ribofuranose (II), and the other involves transribosylation between N4-acylcytosines and acyl-inosines or -guanosines (IVa—d). N4-Octanoyl-2',3',5'-triacetylcytidine (Illf) was converted into cytidine by deacylation in a good yield.

AB - N4-Isobutyryl- and -(2-ethylhexanoyl)cytosines (la, b) were synthesized by acylation of cytosine. Y4,2',3',5'-Tetraacylcytidines (III) were synthesized by two methods involving stannic chloride catalysis. One involves condensation of N4-acylcytosines (I) and l-0-acetyl-2,3,5-tri-0-benzoyl-β-D-ribofuranose (II), and the other involves transribosylation between N4-acylcytosines and acyl-inosines or -guanosines (IVa—d). N4-Octanoyl-2',3',5'-triacetylcytidine (Illf) was converted into cytidine by deacylation in a good yield.

KW - 2',3 ',5 ',-tetraacylcytidine

KW - N4-acylcytosine N4

KW - acylinosine

KW - condensation acylribose

KW - stannic chloride

KW - synthesis acylguanosine

KW - transribosylation

UR - http://www.scopus.com/inward/record.url?scp=0023759499&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0023759499&partnerID=8YFLogxK

U2 - 10.1248/cpb.36.3253

DO - 10.1248/cpb.36.3253

M3 - Article

AN - SCOPUS:0023759499

VL - 36

SP - 3253

EP - 3256

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

SN - 0009-2363

IS - 9

ER -