From adenosine to 3′-deoxyadenosine:: Development and scale up

被引：26

作者：

Aman, S ^{[1
]}

Anderson, DJ ^{[1
]}

Connolly, TJ ^{[1
]}

Crittall, AJ ^{[1
]}

Ji, GJ ^{[1
]}

机构：

[1] Raylo Chem Inc, Edmonton, AB T6C 4A9, Canada

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2000年 / 4卷 / 06期

关键词：

D O I：

10.1021/op000209x

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A manufacturing process has been developed suitable for the production of 3'-deoxyadenosine (cordycepin, 3'-dA) in 20% yield from adenosine, The chemistry involves conversion of adenosine to isomeric 2',3'-bromoacetates with isolation of the desired isomer in high purity. Acidic hydrolysis followed by hydrogenolysis afforded product with a purity of greater than or equal to 99%, Unlike routes reported in the literature, intermediates are isolated as solids, thus avoiding the use of chromatography for isomer separation and final product purification.

引用

页码：601 / 605

页数：5

共 22 条

[1] REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .7. CONVERSION OF THIOCARBONATES INTO DEOXY-SUGARS
BARTON, DHR
SUBRAMANIAN, R
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (15): : 1718 - 1723
[2] BAZIN H, 1985, SYNTHESIS-STUTTGART, P1108
[3] A NEW SYNTHESIS OF 2',3'-DIDEOXYINOSINE
BHAT, V
STOCKER, E
UGARKAR, BG
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (10) : 1481 - 1486
[4] CORDYCEPIN, A METABOLIC PRODUCT FROM CULTURES OF CORDYCEPS-MILITARIS (LINN) LINK .1. ISOLATION AND CHARACTERISATION
CUNNINGHAM, KG
HUTCHINSON, SA
MANSON, W
SPRING, FS
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1951, (SEP): : 2299 - 2300
[5] DORLAND E, 1992, SYNTHESIS-STUTTGART, P477
[6] NUCLEIC-ACID RELATED-COMPOUNDS .49. REGIOSPECIFIC AND STEREOSELECTIVE CONVERSION OF RIBONUCLEOSIDES TO 3'-DEOXYNUCLEOSIDES - A HIGH-YIELD 3-STAGE SYNTHESIS OF CORDYCEPIN FROM ADENOSINE
HANSSKE, F
ROBINS, MJ
[J]. TETRAHEDRON LETTERS, 1985, 26 (36) : 4295 - 4298
[7] A CONVENIENT PREPARATION OF PROTECTED 3'-DEOXYGUANOSINE FROM GUANOSINE
HE, GX
BISCHOFBERGER, N
[J]. TETRAHEDRON LETTERS, 1995, 36 (39) : 6991 - 6994
[8] REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE
HERDEWIJN, P
[J]. TETRAHEDRON, 1989, 45 (20) : 6563 - 6580
[9] CHIRALLY SELECTIVE SYNTHESIS OF SUGAR MOIETY OF NUCLEOSIDES BY CHEMICOENZYMATIC APPROACH - L-RIBOSES AND D-RIBOSES, SHOWDOMYCIN, AND CORDYCEPIN
ITO, Y
SHIBATA, T
ARITA, M
SAWAI, H
OHNO, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) : 6739 - 6741
[10] REACTIONS OF 2-ACYLOXYISOBUTYRYL HALIDES WITH NUCLEOSIDES .4. FACILE SYNTHESIS OF 2',3'-UNSATURATED NUCLEOSIDES USING CHROMOUS ACETATE
JAIN, TC
JENKINS, ID
RUSSELL, AF
VERHEYDE.JP
MOFFATT, JG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (01) : 30 - 38

← 1 2 3 →