Synthesis and crystal structure of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene- β-d-glucopyranose

Marco Brito-Arias; Mariana Beltrán-Magaña; Candy Acosta-Santamaría; Judit Galcera; Elies Molins

doi:10.1007/s10870-009-9594-0

Synthesis and crystal structure of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene- β-d-glucopyranose

Marco Brito-Arias, Mariana Beltrán-Magaña, Candy Acosta-Santamaría, Judit Galcera, Elies Molins

Unidad Profesional Interdisciplinaria de Biotecnología (UPIBI)

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

1 Scopus citations

Abstract

The crystal of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d- glucopyranose (I) was studied by X-ray diffraction. (I) crystallizes in the monoclinic space group P2 ₁ with cell parameters of a = 5.691(3) Å, b = 7.770(2) Å, c = 22.503(7) Å, b = 93.58(5)°, V = 993.1(7) Å³ and Z = 2. The molecular structure of (I) consists of a 4,6-O-benzylidene-glucopyranose moiety which has the 4-OH and 6-OH groups of the glucopyranose protected by glycosidic bonding to a benzylic carbon, forming a benzyl acetal. The other OH groups of the glucopyranose ring are also protected with three acetate groups. In the crystal structure adjacent molecules are linked by C-H•••O hydrogen bonds.

Original language	English
Pages (from-to)	1-3
Number of pages	3
Journal	Journal of Chemical Crystallography
Volume	40
Issue number	1
DOIs	https://doi.org/10.1007/s10870-009-9594-0
State	Published - Jan 2010

Keywords

1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose
Benzylidenes
Crystal structure
O-glycosides

Access to Document

10.1007/s10870-009-9594-0

Cite this

@article{737a208499f047d18ad210ce7f014a14,

title = "Synthesis and crystal structure of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene- β-d-glucopyranose",

abstract = "The crystal of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d- glucopyranose (I) was studied by X-ray diffraction. (I) crystallizes in the monoclinic space group P2 1 with cell parameters of a = 5.691(3) {\AA}, b = 7.770(2) {\AA}, c = 22.503(7) {\AA}, b = 93.58(5)°, V = 993.1(7) {\AA}3 and Z = 2. The molecular structure of (I) consists of a 4,6-O-benzylidene-glucopyranose moiety which has the 4-OH and 6-OH groups of the glucopyranose protected by glycosidic bonding to a benzylic carbon, forming a benzyl acetal. The other OH groups of the glucopyranose ring are also protected with three acetate groups. In the crystal structure adjacent molecules are linked by C-H•••O hydrogen bonds.",

keywords = "1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose, Benzylidenes, Crystal structure, O-glycosides",

author = "Marco Brito-Arias and Mariana Beltr{\'a}n-Maga{\~n}a and Candy Acosta-Santamar{\'i}a and Judit Galcera and Elies Molins",

note = "Funding Information: Acknowledgment. The authors are grateful for financial support from COFAA, SIP-IPN and Generalitat de Catalunya (2005SGR-452).",

year = "2010",

month = jan,

doi = "10.1007/s10870-009-9594-0",

language = "Ingl{\'e}s",

volume = "40",

pages = "1--3",

journal = "Journal of Chemical Crystallography",

issn = "1074-1542",

number = "1",

}

TY - JOUR

T1 - Synthesis and crystal structure of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene- β-d-glucopyranose

AU - Brito-Arias, Marco

AU - Beltrán-Magaña, Mariana

AU - Acosta-Santamaría, Candy

AU - Galcera, Judit

AU - Molins, Elies

N1 - Funding Information: Acknowledgment. The authors are grateful for financial support from COFAA, SIP-IPN and Generalitat de Catalunya (2005SGR-452).

PY - 2010/1

Y1 - 2010/1

N2 - The crystal of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d- glucopyranose (I) was studied by X-ray diffraction. (I) crystallizes in the monoclinic space group P2 1 with cell parameters of a = 5.691(3) Å, b = 7.770(2) Å, c = 22.503(7) Å, b = 93.58(5)°, V = 993.1(7) Å3 and Z = 2. The molecular structure of (I) consists of a 4,6-O-benzylidene-glucopyranose moiety which has the 4-OH and 6-OH groups of the glucopyranose protected by glycosidic bonding to a benzylic carbon, forming a benzyl acetal. The other OH groups of the glucopyranose ring are also protected with three acetate groups. In the crystal structure adjacent molecules are linked by C-H•••O hydrogen bonds.

AB - The crystal of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d- glucopyranose (I) was studied by X-ray diffraction. (I) crystallizes in the monoclinic space group P2 1 with cell parameters of a = 5.691(3) Å, b = 7.770(2) Å, c = 22.503(7) Å, b = 93.58(5)°, V = 993.1(7) Å3 and Z = 2. The molecular structure of (I) consists of a 4,6-O-benzylidene-glucopyranose moiety which has the 4-OH and 6-OH groups of the glucopyranose protected by glycosidic bonding to a benzylic carbon, forming a benzyl acetal. The other OH groups of the glucopyranose ring are also protected with three acetate groups. In the crystal structure adjacent molecules are linked by C-H•••O hydrogen bonds.

KW - 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose

KW - Benzylidenes

KW - Crystal structure

KW - O-glycosides

UR - http://www.scopus.com/inward/record.url?scp=73349139191&partnerID=8YFLogxK

U2 - 10.1007/s10870-009-9594-0

DO - 10.1007/s10870-009-9594-0

M3 - Artículo

SN - 1074-1542

VL - 40

SP - 1

EP - 3

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

IS - 1

ER -

Synthesis and crystal structure of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene- β-d-glucopyranose

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this