Iodonium Ion Promoted Cyclization: A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-manno-2-octulosonic Acid (KDO)

Pieter A.M. Van Der Klein; Geert J.P.H. Boons; Gerrit H. Veeneman; Gijs A. Van Der Marel; Jacques H. Van Boom

doi:10.1055/s-1990-21073

Iodonium Ion Promoted Cyclization: A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-manno-2-octulosonic Acid (KDO)

Pieter A.M. Van Der Klein
, Geert J.P.H. Boons
, Gerrit H. Veeneman
, Gijs A. Van Der Marel
, Jacques H. Van Boom

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Cyclization of methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octulonate diethyl dithioacetal with iodonium sym-dicollidine perchlorate or N-iodosuccinimide yields methyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-2-enulosonate (KDO-glycal) or the ethyl 2-thio-α-glycoside of 3-deoxy-D-manno-2-octulosonic acid, respectively. The latter compounds can be employed as glycosyl donors of 3-deoxy-D-manno-2-octulosonic acid.

Original language	English
Pages (from-to)	311-313
Number of pages	3
Journal	Synlett
Volume	1990
Issue number	6
DOIs	https://doi.org/10.1055/s-1990-21073
Publication status	Published - 1 Jun 1990
Externally published	Yes

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title = "Iodonium Ion Promoted Cyclization: A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-manno-2-octulosonic Acid (KDO)",

abstract = "Cyclization of methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octulonate diethyl dithioacetal with iodonium sym-dicollidine perchlorate or N-iodosuccinimide yields methyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-2-enulosonate (KDO-glycal) or the ethyl 2-thio-α-glycoside of 3-deoxy-D-manno-2-octulosonic acid, respectively. The latter compounds can be employed as glycosyl donors of 3-deoxy-D-manno-2-octulosonic acid.",

author = "\{Van Der Klein\}, \{Pieter A.M.\} and Boons, \{Geert J.P.H.\} and Veeneman, \{Gerrit H.\} and \{Van Der Marel\}, \{Gijs A.\} and \{Van Boom\}, \{Jacques H.\}",

year = "1990",

month = jun,

day = "1",

doi = "10.1055/s-1990-21073",

language = "English",

volume = "1990",

pages = "311--313",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "6",

}

TY - JOUR

T1 - Iodonium Ion Promoted Cyclization

T2 - A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-manno-2-octulosonic Acid (KDO)

AU - Van Der Klein, Pieter A.M.

AU - Boons, Geert J.P.H.

AU - Veeneman, Gerrit H.

AU - Van Der Marel, Gijs A.

AU - Van Boom, Jacques H.

PY - 1990/6/1

Y1 - 1990/6/1

N2 - Cyclization of methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octulonate diethyl dithioacetal with iodonium sym-dicollidine perchlorate or N-iodosuccinimide yields methyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-2-enulosonate (KDO-glycal) or the ethyl 2-thio-α-glycoside of 3-deoxy-D-manno-2-octulosonic acid, respectively. The latter compounds can be employed as glycosyl donors of 3-deoxy-D-manno-2-octulosonic acid.

AB - Cyclization of methyl 3-deoxy-4,5:7,8-di-O-isopropylidene-D-manno-octulonate diethyl dithioacetal with iodonium sym-dicollidine perchlorate or N-iodosuccinimide yields methyl 2,3-dideoxy-4,5:7,8-di-O-isopropylidene-D-manno-oct-2-enulosonate (KDO-glycal) or the ethyl 2-thio-α-glycoside of 3-deoxy-D-manno-2-octulosonic acid, respectively. The latter compounds can be employed as glycosyl donors of 3-deoxy-D-manno-2-octulosonic acid.

UR - https://www.scopus.com/pages/publications/85043763359

U2 - 10.1055/s-1990-21073

DO - 10.1055/s-1990-21073

M3 - Article

AN - SCOPUS:85043763359

SN - 0936-5214

VL - 1990

SP - 311

EP - 313

JO - Synlett

JF - Synlett

IS - 6

ER -

Iodonium Ion Promoted Cyclization: A Convenient Approach to Glycosyl Donors of 3-Deoxy-D-manno-2-octulosonic Acid (KDO)

Abstract

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