Formal Synthesis of 3-Deoxy-D-manno-Octulosonic Acid (KDO) and 3-Deoxy-D-arabino-2-heptulosonic Acid (DAH)

被引：10
|
作者：
Pradhan, Tapan Kumar [1 ]
Lin, Chun Cheng [2 ]
Mong, Kwok Kong Tony [1 ]
机构：
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu, Taiwan
[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan
来源：
SYNLETT | 2013年 / 24卷 / 02期
关键词：
carbohydrates; Wittig; Corey-Fuchs; cyclization; RING-CLOSING METATHESIS; 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID; CHEMICAL-SYNTHESIS; DERIVATIVES; CHEMISTRY; ETHERS; ESTER;
D O I：
10.1055/s-0032-1317932
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Practical synthetic routes to 3-deoxy-D-manno-octulo-sonic acid (KDO) and 3-deoxy-D-arabino-2-heptulosonic acid (DAH) from common sugar substrates are reported. Chain homologation of the sugar substrates was accomplished by Wittig olefination and Corey-Fuchs alkynylation. A new cyclization strategy was investigated to access the desired pyranosyl isomer of the KDO target.
引用
收藏
页码：219 / 222
页数：4
相关论文
共 50 条
  • [31] Synthesis of 3-deoxy-D-manno-2-octulosonic acid (Kdo) and D-glycero-D-talo-2-octulosonic acid (Ko) and their α-glycosides
    Reiner, M
    Schmidt, RR
    [J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (01) : 319 - 335
  • [32] A new short and efficient route to 3-deoxy-D-manno-oct-2-ulosonic acid (KDO) and 3-deoxy-D-arabino-hept-2-ulosonic acid (DAH)
    Kikelj, V
    Plantier-Royon, R
    Portella, C
    [J]. SYNTHESIS-STUTTGART, 2006, 7 (07): : 1200 - 1204
  • [33] A NEW SYNTHESIS OF 3-DEOXY-D-MANNO-OCTULOSONIC ACID ENOLLACTONES THROUGH THIOKETALE DERIVATIVES
    KORNILOV, VI
    ZHDANOV, YA
    MIKSHIEV, YM
    PAYDAK, BB
    MAKAROVA, OM
    [J]. BIOORGANICHESKAYA KHIMIYA, 1987, 13 (05): : 708 - 709
  • [34] Preparation of the phosphonic acid analogue of 3-deoxy-D-manno-2-octulosonic acid (KDO)
    Coutrot, P
    Grison, C
    Lecouvey, M
    [J]. TETRAHEDRON LETTERS, 1996, 37 (10) : 1595 - 1598
  • [35] A NEW SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO) FROM D-MANNOSE
    IMOTO, M
    KUSUMOTO, S
    SHIBA, T
    [J]. TETRAHEDRON LETTERS, 1987, 28 (49) : 6235 - 6238
  • [36] STUDIES OF THE SYNTHESIS OF SUGAR PHOSPHONATES RELATED TO 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    MOLIN, H
    NOREN, JO
    CLAESSON, A
    [J]. CARBOHYDRATE RESEARCH, 1989, 194 : 209 - 221
  • [37] 3-Deoxy-D-manno-octulosonic Acid (Kdo) Hydrolase Identified in Francisella tularensis, Helicobacter pylori, and Legionella pneumophila
    Chalabaev, Sabina
    Kim, Tae-Hyun
    Ross, Robin
    Derian, Alec
    Kasper, Dennis L.
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (45) : 34330 - 34336
  • [38] VINYL CARBANIONS .19. SYNTHESIS OF 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
    SCHMIDT, RR
    BETZ, R
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (06): : 430 - 431
  • [39] Histidine 268 in 3-deoxy-D-arabino-heptulosonic acid 7-phosphate synthase plays the same role as histidine 202 in 3-deoxy-D-manno-octulosonic acid 8-phosphate synthase
    Howe, DL
    Duewel, HS
    Woodard, RW
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (51) : 40258 - 40265
  • [40] Synthesis of 4,5-disubstituted-3-deoxy-D-manno-octulosonic acid (Kdo) derivatives
    Yi, Ruiqin
    Ogaki, Atsushi
    Fukunaga, Mayumi
    Nakajima, Hiromitsu
    Ichiyanagi, Tsuyoshi
    [J]. TETRAHEDRON, 2014, 70 (23) : 3675 - 3682
12345