(2s,3r,6r)-2-[(r)-1-hydroxyallyl]-4, 4-dimethoxy-6-methyltetrahydro-2h-pyran-3-ol

Jack Bennett; Paul V. Murphy

doi:10.3390/M1140

(2s,3r,6r)-2-[(r)-1-hydroxyallyl]-4, 4-dimethoxy-6-methyltetrahydro-2h-pyran-3-ol

Jack Bennett
, Paul V. Murphy

Infectious Disease

University of Galway

Research output: Contribution to a Journal (Peer & Non Peer) › Article › peer-review

Abstract

(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1, 8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by¹H and¹³C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

Original language	English
Article number	M1140
Pages (from-to)	1-5
Number of pages	5
Journal	MolBank
Volume	2020
Issue number	2
DOIs	https://doi.org/10.3390/M1140
Publication status	Published - Jun 2020

Keywords

Cyclisation
Deprotection
Functionalized scaffold
Glucose
Tetrahydropyran

Access to Document

10.3390/M1140

Cite this

@article{dd6626bad22d49008ab702c11558d657,

title = "(2s,3r,6r)-2-[(r)-1-hydroxyallyl]-4, 4-dimethoxy-6-methyltetrahydro-2h-pyran-3-ol",

abstract = "(2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18\% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1, 8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by1H and13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.",

keywords = "Cyclisation, Deprotection, Functionalized scaffold, Glucose, Tetrahydropyran",

author = "Jack Bennett and Murphy, \{Paul V.\}",

note = "Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2020",

month = jun,

doi = "10.3390/M1140",

language = "English",

volume = "2020",

pages = "1--5",

journal = "MolBank",

issn = "1422-8599",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "2",

}

TY - JOUR

T1 - (2s,3r,6r)-2-[(r)-1-hydroxyallyl]-4, 4-dimethoxy-6-methyltetrahydro-2h-pyran-3-ol

AU - Bennett, Jack

AU - Murphy, Paul V.

PY - 2020/6

Y1 - 2020/6

N2 - (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1, 8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by1H and13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

AB - (2S,3R,6R)-2-[(R)-1-Hydroxyallyl]-4,4-dimethoxy-6-methyltetrahydro-2H-pyran-3-ol was isolated in 18% after treating the glucose derived (5R,6S,7R)-5,6,7-tris[(triethylsilyl)oxy]nona-1, 8-dien-4-one with (1S)-(+)-10-camphorsulfonic acid (CSA). The one-pot formation of the title compound involved triethylsilyl (TES) removal, alkene isomerization, intramolecular conjugate addition and ketal formation. The compound was characterized by1H and13C NMR spectroscopy, ESI mass spectrometry and IR spectroscopy. NMR spectroscopy was used to establish the product structure, including the conformation of its tetrahydropyran ring.

KW - Cyclisation

KW - Deprotection

KW - Functionalized scaffold

KW - Glucose

KW - Tetrahydropyran

UR - https://www.scopus.com/pages/publications/85086150529

U2 - 10.3390/M1140

DO - 10.3390/M1140

M3 - Article

AN - SCOPUS:85086150529

SN - 1422-8599

VL - 2020

SP - 1

EP - 5

JO - MolBank

JF - MolBank

IS - 2

M1 - M1140

ER -

(2s,3r,6r)-2-[(r)-1-hydroxyallyl]-4, 4-dimethoxy-6-methyltetrahydro-2h-pyran-3-ol

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this