Crystal structure and absolute configuration of methyl 3,4-di-O-acetyl-6- deoxy-6-iodo-2-O-p-tolylsulphonyl-α-D-mannopyranoside

Mazhar-Ul-Haque; Ali Freestone

doi:10.1039/P29770001509

Crystal structure and absolute configuration of methyl 3,4-di-O-acetyl-6- deoxy-6-iodo-2-O-p-tolylsulphonyl-α-D-mannopyranoside

Mazhar-Ul-Haque^*
, Ali Freestone

^*Corresponding author for this work

King Fahd University of Petroleum & Minerals

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

4 Scopus citations

Abstract

The title compound (7) was isolated as a minor product of successive tosylation, acetylation and iodide displacement of methyl α-D- mannopyranoside (1). Crystals of the title compound are orthorhombic, space group P2₁2₁2₁, a = 9.293(2), b = 14.220(6), c = 16.969(6) Å, Z = 4. The structure was solved from diffractometer data by heavy-atom techniques, and refined by block-diagonal least-squares methods to R 0.052 for 1 802 independent reflections. The results supply the constitution and absolute configuration (8). The conformation of the pyranoside ring is ⁴C₁ (≡C1) in the solid state and ¹H n.m.r. studies showed this to be the predominant conformation in solution also.

Original language	English
Pages (from-to)	1509-1513
Number of pages	5
Journal	Journal of the Chemical Society. Perkin Transactions 2
Issue number	12
DOIs	https://doi.org/10.1039/P29770001509
State	Published - 1977

Bibliographical note

Funding Information:
In our case O(20) carries a methyl group but the C(1)-O(20) bond is still the shortest (1.39 A).The carbon valence angles within the pyranose ring vary from 107.6 to 111.9(8) [mean 109.4(8)"] ; the angle at O(19) is 114.7(7), which is larger than the tetrahedral l5 G. Strahs, Adv.Carbohydrate Chem. Biochem., 1970, 25, 53, and refs. therein. l6 H. McD. McGeachin and C. A. Beevers, Acta Cryst., 1957,10, 227. l7 A. Hordvick, Acta Chem. Scand., 1961,15, 16. not deviate significantly from their standard values. Intermolecular contacts G3.6 A are given in Table 5. None of them are especially short and are normal van der Waals contacts. The shortest contact between iodine and O(27) is 3.27 A. We thank the University of Petroleum and Minerals for a research grant (to M. U. H.), and the staff of the Com-puter Centre for their co-operation. [6/1618 Received, 19th August, 19761 l8 W. G. Ferrier, Acta Cryst., 1963, 16, 1023. l9 J. H. Robertson and B. Sheldrick, Acta Cryst., 1965,19, 820. 2o R. Hoge and J. Trotter, J. Chem. Soc. (A), 1968, 267. 21 ' Molecular Structures and Dimensions,' vol. A, eds. 0. Kennard and D. G. Watson, 1972, Oesthock, Utrecht, p. S2.

ASJC Scopus subject areas

General Chemistry

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Cite this

@article{fb9cf6c3d74b41809bfdafc33034b187,

title = "Crystal structure and absolute configuration of methyl 3,4-di-O-acetyl-6- deoxy-6-iodo-2-O-p-tolylsulphonyl-α-D-mannopyranoside",

abstract = "The title compound (7) was isolated as a minor product of successive tosylation, acetylation and iodide displacement of methyl α-D- mannopyranoside (1). Crystals of the title compound are orthorhombic, space group P212121, a = 9.293(2), b = 14.220(6), c = 16.969(6) {\AA}, Z = 4. The structure was solved from diffractometer data by heavy-atom techniques, and refined by block-diagonal least-squares methods to R 0.052 for 1 802 independent reflections. The results supply the constitution and absolute configuration (8). The conformation of the pyranoside ring is 4C1 (≡C1) in the solid state and 1H n.m.r. studies showed this to be the predominant conformation in solution also.",

author = "Mazhar-Ul-Haque and Ali Freestone",

note = "Funding Information: In our case O(20) carries a methyl group but the C(1)-O(20) bond is still the shortest (1.39 A).The carbon valence angles within the pyranose ring vary from 107.6 to 111.9(8) [mean 109.4(8){"}] ; the angle at O(19) is 114.7(7), which is larger than the tetrahedral l5 G. Strahs, Adv.Carbohydrate Chem. Biochem., 1970, 25, 53, and refs. therein. l6 H. McD. McGeachin and C. A. Beevers, Acta Cryst., 1957,10, 227. l7 A. Hordvick, Acta Chem. Scand., 1961,15, 16. not deviate significantly from their standard values. Intermolecular contacts G3.6 A are given in Table 5. None of them are especially short and are normal van der Waals contacts. The shortest contact between iodine and O(27) is 3.27 A. We thank the University of Petroleum and Minerals for a research grant (to M. U. H.), and the staff of the Com-puter Centre for their co-operation. [6/1618 Received, 19th August, 19761 l8 W. G. Ferrier, Acta Cryst., 1963, 16, 1023. l9 J. H. Robertson and B. Sheldrick, Acta Cryst., 1965,19, 820. 2o R. Hoge and J. Trotter, J. Chem. Soc. (A), 1968, 267. 21 ' Molecular Structures and Dimensions,' vol. A, eds. 0. Kennard and D. G. Watson, 1972, Oesthock, Utrecht, p. S2.",

year = "1977",

doi = "10.1039/P29770001509",

language = "English",

pages = "1509--1513",

journal = "Journal of the Chemical Society. Perkin Transactions 2",

issn = "0300-9580",

publisher = "Chemical Society",

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T1 - Crystal structure and absolute configuration of methyl 3,4-di-O-acetyl-6- deoxy-6-iodo-2-O-p-tolylsulphonyl-α-D-mannopyranoside

AU - Mazhar-Ul-Haque,

AU - Freestone, Ali

N1 - Funding Information: In our case O(20) carries a methyl group but the C(1)-O(20) bond is still the shortest (1.39 A).The carbon valence angles within the pyranose ring vary from 107.6 to 111.9(8) [mean 109.4(8)"] ; the angle at O(19) is 114.7(7), which is larger than the tetrahedral l5 G. Strahs, Adv.Carbohydrate Chem. Biochem., 1970, 25, 53, and refs. therein. l6 H. McD. McGeachin and C. A. Beevers, Acta Cryst., 1957,10, 227. l7 A. Hordvick, Acta Chem. Scand., 1961,15, 16. not deviate significantly from their standard values. Intermolecular contacts G3.6 A are given in Table 5. None of them are especially short and are normal van der Waals contacts. The shortest contact between iodine and O(27) is 3.27 A. We thank the University of Petroleum and Minerals for a research grant (to M. U. H.), and the staff of the Com-puter Centre for their co-operation. [6/1618 Received, 19th August, 19761 l8 W. G. Ferrier, Acta Cryst., 1963, 16, 1023. l9 J. H. Robertson and B. Sheldrick, Acta Cryst., 1965,19, 820. 2o R. Hoge and J. Trotter, J. Chem. Soc. (A), 1968, 267. 21 ' Molecular Structures and Dimensions,' vol. A, eds. 0. Kennard and D. G. Watson, 1972, Oesthock, Utrecht, p. S2.

PY - 1977

Y1 - 1977

N2 - The title compound (7) was isolated as a minor product of successive tosylation, acetylation and iodide displacement of methyl α-D- mannopyranoside (1). Crystals of the title compound are orthorhombic, space group P212121, a = 9.293(2), b = 14.220(6), c = 16.969(6) Å, Z = 4. The structure was solved from diffractometer data by heavy-atom techniques, and refined by block-diagonal least-squares methods to R 0.052 for 1 802 independent reflections. The results supply the constitution and absolute configuration (8). The conformation of the pyranoside ring is 4C1 (≡C1) in the solid state and 1H n.m.r. studies showed this to be the predominant conformation in solution also.

AB - The title compound (7) was isolated as a minor product of successive tosylation, acetylation and iodide displacement of methyl α-D- mannopyranoside (1). Crystals of the title compound are orthorhombic, space group P212121, a = 9.293(2), b = 14.220(6), c = 16.969(6) Å, Z = 4. The structure was solved from diffractometer data by heavy-atom techniques, and refined by block-diagonal least-squares methods to R 0.052 for 1 802 independent reflections. The results supply the constitution and absolute configuration (8). The conformation of the pyranoside ring is 4C1 (≡C1) in the solid state and 1H n.m.r. studies showed this to be the predominant conformation in solution also.

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DO - 10.1039/P29770001509

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SN - 0300-9580

SP - 1509

EP - 1513

JO - Journal of the Chemical Society. Perkin Transactions 2

JF - Journal of the Chemical Society. Perkin Transactions 2

IS - 12

ER -

Crystal structure and absolute configuration of methyl 3,4-di-O-acetyl-6- deoxy-6-iodo-2-O-p-tolylsulphonyl-α-D-mannopyranoside

Abstract

Bibliographical note

ASJC Scopus subject areas

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