CHEMOENZYMATIC SYNTHESIS OF (-)-CARBOCYCLIC 7-DEAZAOXETANOCIN-G

被引：22

作者：

CHEN, X ^{[1
]}

SIDDIQI, SM ^{[1
]}

SCHNELLER, SW ^{[1
]}

机构：

[1] UNIV S FLORIDA,DEPT CHEM,TAMPA,FL 33620

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(00)74181-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective synthesis of (-)-(1R,2S,3S)-2-amino-7-[2,3-bis(hydroxymethyl)-cyclobutyl]pyrrolo[2,3-d]pyrimidin-4(3H)-one (5) as the 7-deaza analogue of carbocyclic oxetanocin G is described in 13 steps from trans-3,3-diethoxy-1,2-bis(hydroxymethyl)cyclobutane (8) in an overall yield of 6%. Included in this route is the use of Pseudomonas cepacia lipase for enzymatic resolution.

引用

页码：2249 / 2252

页数：4

共 19 条

[1] SYNTHESIS AND ANTIVIRAL ACTIVITY OF ENANTIOMERIC FORMS OF CYCLOBUTYL NUCLEOSIDE ANALOGS
BISACCHI, GS
BRAITMAN, A
CIANCI, CW
CLARK, JM
FIELD, AK
HAGEN, ME
HOCKSTEIN, DR
MALLEY, MF
MITT, T
SLUSARCHYK, WA
SUNDEEN, JE
TERRY, BJ
TUOMARI, AV
WEAVER, ER
YOUNG, MG
ZAHLER, R
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (04) : 1415 - 1421
[2] DAVIES HG, 1989, BIOTRANSFORMATIONS P
[3] (+/-)-(1-ALPHA,2-BETA,3-ALPHA)-9-[2,3-BIS(HYDROXYMETHYL)-CYCLOBUTYL]GUANINE [(+/-)-BHCG OR SQ 33054] - A POTENT AND SELECTIVE INHIBITOR OF HERPESVIRUSES
FIELD, AK
TUOMARI, AV
MCGEEVERRUBIN, B
TERRY, BJ
MAZINA, KE
HAFFEY, ML
HAGEN, ME
CLARK, JM
BRAITMAN, A
SLUSARCHYK, WA
YOUNG, MG
ZAHLER, R
[J]. ANTIVIRAL RESEARCH, 1990, 13 (01) : 41 - 52
[4] CYCLOBUT-A AND CYCLOBUT-G, CARBOCYCLIC OXETANOCIN ANALOGS THAT INHIBIT THE REPLICATION OF HUMAN-IMMUNODEFICIENCY-VIRUS IN T-CELLS AND MONOCYTES AND MACROPHAGES INVITRO
HAYASHI, S
NORBECK, DW
ROSENBROOK, W
FINE, RL
MATSUKURA, M
PLATTNER, JJ
BRODER, S
MITSUYA, H
[J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1990, 34 (02) : 287 - 294
[5] HONJO M, 1989, CHEM PHARM BULL, V37, P1413
[6] INHIBITION OF INFECTIVITY OF HUMAN-IMMUNODEFICIENCY-VIRUS BY OXETANOCIN
HOSHINO, H
SHIMIZU, N
SHIMADA, N
TAKITA, T
TAKEUCHI, T
[J]. JOURNAL OF ANTIBIOTICS, 1987, 40 (07) : 1077 - 1078
[7] EFFICIENT SYNTHESES OF PROTECTED (2S,3S)-2,3-BIS(HYDROXYMETHYL)CYCLOBUTANONE, KEY INTERMEDIATES FOR THE SYNTHESIS OF CHIRAL CARBOCYCLIC ANALOGS OF OXETANOCIN
HSIAO, CN
HANNICK, SM
[J]. TETRAHEDRON LETTERS, 1990, 31 (46) : 6609 - 6612
[8] LIPASE-CATALYZED ASYMMETRIC HYDROLYSIS OF ESTERS HAVING REMOTE CHIRAL PROCHIRAL CENTERS
HUGHES, DL
BERGAN, JJ
AMATO, JS
BHUPATHY, M
LEAZER, JL
MCNAMARA, JM
SIDLER, DR
REIDER, PJ
GRABOWSKI, EJJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) : 6252 - 6259
[9] ENANTIO-SELECTIVE AND DIASTEREO-SELECTIVE SYNTHESIS OF CARBOCYCLIC OXETANOCIN ANALOGS
ICHIKAWA, Y
NARITA, A
SHIOZAWA, A
HAYASHI, Y
NARASAKA, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (24) : 1919 - 1921
[10] CARBOCYCLIC NUCLEOSIDES
MARQUEZ, VE
LIM, MI
[J]. MEDICINAL RESEARCH REVIEWS, 1986, 6 (01) : 1 - 40

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