Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal)

Ivan A. Gagarinov; Apoorva D. Srivastava; Geert Jan Boons; Satsawat Visansirikul

doi:10.1201/9781315120300-24

Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal)

Ivan A. Gagarinov^*
, Apoorva D. Srivastava
, Geert Jan Boons
, Satsawat Visansirikul

^*Corresponding author for this work

University of Missouri at St. Louis

Research output: Chapter in Book/Report/Conference proceeding › Chapter › Academic › peer-review

Abstract

196 N-Acetyl-d-fucosamine (d-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. ¹ Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected d-FucNAc-derived building blocks, which are available from diverse precursors. ² Azidonitration of the title 3, 4-di-O-acetyl-D-fucal^{2b, 3} (3, 4-di-O-acetyl-1, 5-anhydro-2, 6-dideoxy-d-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of d-fucosamine and derivatives thereof. Accessing the title compound ³ on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34%-40% overall yield, starting from commercially available 1, 2:3, 4-di-O-isopropylidene-d-galactose.

Original language	English
Title of host publication	Carbohydrate Chemistry
Editors	Christian Vogel, Paul Murphy
Place of Publication	Boca Raton
Publisher	CRC Press
Chapter	24
Pages	195-200
Number of pages	6
ISBN (Electronic)	9781315120300
ISBN (Print)	9781498726917
DOIs	https://doi.org/10.1201/9781315120300-24
Publication status	Published - 5 Oct 2017

Publication series

Name	Proven Synthetic Methods
Publisher	CRC Press
Volume	4

Bibliographical note

Publisher Copyright:
© 2018 by Taylor and Francis Group, LLC.

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10.1201_9781315120300-24_chapterpdfFinal published version, 922 KBLicence: Taverne

Cite this

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title = "Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal)",

abstract = "196 N-Acetyl-d-fucosamine (d-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. 1 Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected d-FucNAc-derived building blocks, which are available from diverse precursors. 2 Azidonitration of the title 3, 4-di-O-acetyl-D-fucal2b, 3 (3, 4-di-O-acetyl-1, 5-anhydro-2, 6-dideoxy-d-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of d-fucosamine and derivatives thereof. Accessing the title compound 3 on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34\%-40\% overall yield, starting from commercially available 1, 2:3, 4-di-O-isopropylidene-d-galactose.",

author = "Gagarinov, \{Ivan A.\} and Srivastava, \{Apoorva D.\} and Boons, \{Geert Jan\} and Satsawat Visansirikul",

note = "Publisher Copyright: {\textcopyright} 2018 by Taylor and Francis Group, LLC.",

year = "2017",

month = oct,

day = "5",

doi = "10.1201/9781315120300-24",

language = "English",

isbn = "9781498726917",

series = "Proven Synthetic Methods",

publisher = "CRC Press",

pages = "195--200",

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booktitle = "Carbohydrate Chemistry",

}

Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal). / Gagarinov, Ivan A.; Srivastava, Apoorva D.; Boons, Geert Jan et al.
Carbohydrate Chemistry. ed. / Christian Vogel; Paul Murphy. Boca Raton: CRC Press, 2017. p. 195-200 (Proven Synthetic Methods; Vol. 4).

Research output: Chapter in Book/Report/Conference proceeding › Chapter › Academic › peer-review

TY - CHAP

T1 - Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal)

AU - Gagarinov, Ivan A.

AU - Srivastava, Apoorva D.

AU - Boons, Geert Jan

AU - Visansirikul, Satsawat

PY - 2017/10/5

Y1 - 2017/10/5

N2 - 196 N-Acetyl-d-fucosamine (d-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. 1 Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected d-FucNAc-derived building blocks, which are available from diverse precursors. 2 Azidonitration of the title 3, 4-di-O-acetyl-D-fucal2b, 3 (3, 4-di-O-acetyl-1, 5-anhydro-2, 6-dideoxy-d-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of d-fucosamine and derivatives thereof. Accessing the title compound 3 on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34%-40% overall yield, starting from commercially available 1, 2:3, 4-di-O-isopropylidene-d-galactose.

AB - 196 N-Acetyl-d-fucosamine (d-FucNAc) is a rare sugar found in a variety of bacterial glycoconjugates. 1 Chemical synthesis of their repeating units heavily relies on the use of orthogonally protected d-FucNAc-derived building blocks, which are available from diverse precursors. 2 Azidonitration of the title 3, 4-di-O-acetyl-D-fucal2b, 3 (3, 4-di-O-acetyl-1, 5-anhydro-2, 6-dideoxy-d-lyxo-hex-1-enitol) has been routinely used in this laboratory to produce large quantities (>20.0 g) of d-fucosamine and derivatives thereof. Accessing the title compound 3 on a large scale from commercially available d-fucose is prohibitively expensive. We have developed a convenient, six-step procedure to produce this valuable compound in 34%-40% overall yield, starting from commercially available 1, 2:3, 4-di-O-isopropylidene-d-galactose.

UR - https://www.scopus.com/pages/publications/85135969873

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M3 - Chapter

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SN - 9781498726917

T3 - Proven Synthetic Methods

SP - 195

EP - 200

BT - Carbohydrate Chemistry

A2 - Vogel, Christian

A2 - Murphy, Paul

PB - CRC Press

CY - Boca Raton

ER -

Simplifying Access to 3, 4-Di-O-acetyl-1, 5 anhydro-2, 6-dideoxy-D- lyxo-hex-1-enitol (3, 4-Di-O-acetyl-d-fucal)

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