A short synthesis of protected 3-deoxy-D-arabino-2-heptulosonates (DAH) from shikimic acid based on silyl group migration

被引：1

作者：

Gonda, Jozef ^{[1
]}

Psotka, Miroslav ^{[2
]}

Martinkova, Miroslava ^{[1
]}

Fazekasova, Simona ^{[1
]}

Mitrikova, Tatiana ^{[1
]}

Vilkova, Maria ^{[1
]}

机构：

[1] Safarik Univ, Dept Organ Chem, Moyzesova 11, Kosice 04001, Slovakia

[2] Univ Hosp Hradec Kralove, Biomed Res Ctr, Sokolska 581, Hradec Kralove 50005, Czech Republic

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 52期

关键词：

Oxoheptanals; Heptulosonates; Silyl group migration; Shikimic acid; PATHWAY ENZYMES; TARGETS;

D O I：

10.1016/j.tetlet.2018.11.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of (2S,3S,4R)-2,3,4,7-tetrahydroxy-6-oxoheptanals with lower alcohols produced protected 3-deoxy-D-arabino-2-heptulosonates. The key transformation is based on an 1,4-O-O silyl group migration, followed by 6-exo-trig cyclisation to give the final pyranose. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：4620 / 4621

页数：2

共 50 条

[11] CHEMOENZYMATIC SYNTHESIS OF 3-DEOXY-D-ARABINO-HEPTULOSONIC ACID FROM CYCLOHEPTATRIENE
JOHNSON, CR
KOZAK, J
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10): : 2910 - 2912
[12] SYNTHESIS OF A 3-DEOXY-D-ARABINO-2-HEPTULOSONIC ACID-DERIVATIVE
DEVIANNE, G
ESCUDIER, JM
BALTAS, M
GORRICHON, L
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22): : 7343 - 7347
[13] SYNTHESIS OF 3-DEOXY-D-ARABINO-2-HEPTULOSONIC ACID 7-PHOSPHATE BY PHOSPHORYLATION OF METHYL (METHYL 3-DEOXY-D-ARABINO-HEPTULOPYRANOSID)ONATE
ADLERSBERG, M
SPRINSON, DB
CARBOHYDRATE RESEARCH, 1984, 127 (01) : 9 - 14
[14] CHEMISTRY OF 5-YLIDENE-1,3-DIOXOLAN-4-ONES - SYNTHESES OF 3-DEOXY-D-ARABINO-2-HEPTULOSONIC ACID (DAH) AND 3-DEOXY-D-MANNO-2-OCTULOSONIC ACID (KDO)
RAMAGE, R
ROSE, GW
MACLEOD, AM
TETRAHEDRON LETTERS, 1988, 29 (38) : 4877 - 4880
[15] Efficient synthesis of 3-deoxy-D-arabino-2-heptulosonate (DAH) and -D-gluco-2-heptulosonate by a two-carbon chain elongation of D-arabinose
Reiner, M
Stolz, F
Schmidt, RR
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (01) : 57 - 60
[16] 2-DEOXY-D-RIBOSE .6. PREPARATION OF DERIVATIVES OF 3-DEOXY-D-RIBO-HEXONIC ACID AND 3-DEOXY-D-ARABINO-HEXONIC ACID THEREFROM - SOME OBSERVATIONS ON KILIANI SYNTHESIS
WOOD, HB
FLETCHER, HG
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (06): : 1969 - &
[17] SYNTHESIS OF PHOSPHONO ANALOGS OF 3-DEOXY-D-ARABINO-HEPT-2-ULOSONIC ACID 7-PHOSPHATE
LEMARECHAL, P
FROUSSIOS, C
LEVEL, M
AZERAD, R
CARBOHYDRATE RESEARCH, 1981, 94 (01) : 1 - 10
[18] PHOTOCHEMICALLY BASED SYNTHESIS OF DEOXY SUGARS - SYNTHESIS OF 2-DEOXY-D-ARABINO-HEXOPYRANOSE (2-DEOXY-D-GLUCOSE) AND SEVERAL OF ITS DERIVATIVES FROM 3,4,6-TRI-O-ACETYL-D-GLUCAL
BINKLEY, RW
BANKAITIS, D
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1982, 1 (01) : 1 - 8
[19] SYNTHESIS OF NATURAL 3-DEOXY-D-ARABINO-HEPTULOSONIC ACID FROM 2,3-ANHYDRO-2-CHLORO-4,5-6,7-DI-O-CYCLOHEXYLIDENE-D-ARABINO-METHYLHEPTONATE
KORNILOV, VI
BICHEROVA, II
TURIK, SV
ZHDANOV, YA
BIOORGANICHESKAYA KHIMIYA, 1988, 14 (07): : 938 - 943
[20] SYNTHESIS OF 3-DEOXY-4-ORTHO-METHYL-D-ARABINO-2-HEPTULOSONIC ACID AND ITS BEHAVIOR IN WARREN REACTION
CHARON, D
SZABO, L
CARBOHYDRATE RESEARCH, 1974, 34 (02) : 271 - 277

← 1 2 3 4 5 →