Stereoselective synthesis of 3-hydroxymethyl-D-cyclopentenone, the versatile intermediate for the synthesis of carbocyclic nucleosides

被引：1

作者：

Choi, WJ ^{[1
]}

Moon, HR

Kim, HO

Ko, YM

Kim, HJ

Lee, JA

Lee, KM

Yun, MK

Shin, DH

Chun, MW

Sheen, YY

Kim, K

Jeong, LS

机构：

[1] Ewha Womans Univ, Med Chem Lab, Coll Pharm, Seoul 120750, South Korea

[2] Pusan Natl Univ, Coll Pharm, Pusan 609735, South Korea

[3] Seoul Natl Univ, Coll Pharm, Seoul, South Korea

来源：

NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2005年 / 24卷 / 5-7期

关键词：

3-hydroxymethyl-D-cyclopentenone; carbocyclic nucleosides;

D O I：

10.1081/NCN-200061832

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The preparative and stereoselective synthesis (45 - 50% overall yields, >50 g scale) of the key carbasugars 7a-d was achieved from D-ribose via stereoselective Grignard reaction and oxidative rearrangement as key reactions.

引用

页码：611 / 613

页数：3

共 50 条

[21] SYNTHESIS OF CARBOCYCLIC NUCLEOSIDES AND NUCLEOTIDES
CERMAK, R
VINCE, R
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 185 (MAR): : 37 - CARB
[22] Progress in the Synthesis of Carbocyclic Nucleosides
Fan, Xue-Sen
Zhang, Xin-Yang
Wang, Xia
Qu, Gui-Rong
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (11) : 1888 - 1898
[23] SYNTHESIS OF CYCLOPROPYL CARBOCYCLIC NUCLEOSIDES
ZHAO, YF
YANG, TF
NEWTON, MG
CHU, CK
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 86 - CARB
[24] Stereoselective Synthesis of (S)- and (N)-Cyclopropyl-Fused Carbocyclic Nucleosides Using Stereoselective Cyclopropanation
Hyun, Young Eum
Kim, Hong-Rae
Jeong, Lak Shin
JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14): : 9828 - 9837
[25] REGIOSELECTIVE AND STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC 2',3'-DIDEOXY-3'-FLUORO NUCLEOSIDES AS POTENTIAL ANTIVIRAL AGENTS
NAKAYAMA, T
MATSUMURA, Y
MORIZAWA, Y
YASUDA, A
UCHIDA, K
TAKASE, H
MURAKAMI, Y
ATARASHI, S
IKEUCHI, T
OSADA, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 1994, 42 (02) : 183 - 187
[26] SYNTHESIS OF NUCLEOSIDES AND THEIR RELATED-COMPOUNDS .16. HIGHLY STEREOSELECTIVE SYNTHESIS OF CARBOCYCLIC ANALOGS OF OXETANOCIN
KATAGIRI, N
SATO, H
KANEKO, C
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (01) : 288 - 290
[27] SYNTHESIS OF CARBOCYCLIC 2',3'-DIDEOXY-2'-C-HYDROXYMETHYL NUCLEOSIDES AS POTENTIAL INHIBITORS OF HIV
ROSENQUIST, A
KVARNSTROM, I
SVENSSON, SCT
CLASSON, B
SAMUELSSON, B
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (07): : 1779 - 1782
[28] Facile preparation of α-acyloxyacetaldehyde, a versatile intermediate in the synthesis of antiviral nucleosides
Du, JF
Watanabe, KA
SYNTHETIC COMMUNICATIONS, 2004, 34 (11) : 1925 - 1930
[29] Advances in the enantioselective synthesis of carbocyclic nucleosides
Boutureira, Omar
Isabel Matheu, M.
Diaz, Yolanda
Castillon, Sergio
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) : 5056 - 5072
[30] Practical synthesis of D- and L-2-cyclopentenone and their utility for the synthesis of carbocyclic antiviral nucleosides against orthopox viruses (smallpox, monkeypox, and cowpox virus)
Jin, YH
Liu, P
Wang, JN
Baker, R
Huggins, J
Chu, CK
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 9012 - 9018

← 1 2 3 4 5 →