Reagent Controlled Direct Dehydrative Glycosylation with 2-Deoxy Sugars: Construction of the Saquayamycin Z Pentasaccharide

被引：22

作者：

Mizia, J. Colin ^{[1
]}

Bennett, Clay S. ^{[1
]}

机构：

[1] Tufts Univ, Dept Chem, Medford, MA 02155 USA

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 15期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

DE-NOVO SYNTHESIS; MICROMONOSPORA SP TU-6368; ONE-POT SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; HEXASACCHARIDE FRAGMENT; SECONDARY METABOLITES; GALTAMYCIN-B; LANDOMYCIN-A; GLYCOSIDES; RIBOFURANOSYLLUMICHROME;

D O I：

10.1021/acs.orglett.9b02056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of the pentasaccharide fragment of the angucycline antibiotic saquayamycin Z is described. By using our sulfonyl chloride mediated reagent controlled dehydrative glycosylation, we are able to assemble the glycosidic linkages with high levels of anomeric selectivity. The total synthesis was completed in 25 total steps, and in 2.5% overall yield with a longest linear sequence of 15 steps.

引用

页码：5922 / 5927

页数：6

共 15 条

[1] Reagent Controlled β-Specific Dehydrative Glycosylation Reactions with 2-Deoxy-Sugars
Issa, John Paul
Lloyd, Dina
Steliotes, Emily
Bennett, Clay S.
ORGANIC LETTERS, 2013, 15 (16) : 4170 - 4173
[2] Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy Sugars: Construction of the Arugomycin Tetrasaccharide
Romeo, Joseph R.
McDermott, Luca
Bennett, Clay S.
ORGANIC LETTERS, 2020, 22 (09) : 3649 - 3654
[3] DIRECT GLYCOSYLATION OF INDOLE WITH 2-DEOXY RIBOSE
HUYNHDINH, T
BAYARD, MJ
IGOLEN, J
COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1976, 283 (05): : 227 - 228
[4] Reagent-controlled SN2-glycosylation for the direct synthesis of β-linked 2-deoxy-sugars
Issa, John P.
Bennett, Clay S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[5] A Reagent-Controlled SN2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars
Issa, John Paul
Bennett, Clay S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) : 5740 - 5744
[6] A Reagent-Controlled SN2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars
Issa, John Paul
Bennett, Clay S.
SYNTHESIS-STUTTGART, 2014, 46 (15): : A106 - A107
[7] Cyclopropenium mediated dehydrative glycosylations of 2-deoxy sugars and its application to the construction of α-linked 2-deoxy-containing carbohydrate structures
Nogueira, Jason
Bennett, Clay
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 250
[8] Direct and stereoselective synthesis of biologically significant 2-deoxy sugars
Zhu, Jianglong
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
[9] Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation
Ghosh, Titli
Mukherji, Ananya
Srivastava, Hemant Kumar
Kancharla, Pavan K.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (16) : 2870 - 2875
[10] Reagent-Controlled α-Selective Dehydrative Glycosylation of 2,6-Dideoxy- and 2,3,6-Trideoxy Sugars
Nogueira, Jason M.
Bylsma, Marissa
Bright, Danielle K.
Bennett, Clay S.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (34) : 10088 - 10092

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