One-Flask Syntheses of 6-Thioguanosine and 2′-Deoxy-6-Thioguanosine

Pei Pei Kung; Roger A. Jones

doi:10.1016/0040-4039(91)80589-X

One-Flask Syntheses of 6-Thioguanosine and 2′-Deoxy-6-Thioguanosine

Pei Pei Kung, Roger A. Jones

School of Arts and Sciences, Chemistry & Chemical Biology

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

31 Scopus citations

Abstract

We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.¹ We now report high-yield conversion of guanosine and 2′-deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,² then gives the 2-aminopurine nucleosides.

Original language	English (US)
Pages (from-to)	3919-3922
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	32
DOIs	https://doi.org/10.1016/0040-4039(91)80589-X
State	Published - Aug 5 1991

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
2′-deoxy-6-thioguanosine
6-Thioguanosine

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10.1016/0040-4039(91)80589-X

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title = "One-Flask Syntheses of 6-Thioguanosine and 2′-Deoxy-6-Thioguanosine",

abstract = "We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2′-deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.",

keywords = "2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine, 2′-deoxy-6-thioguanosine, 6-Thioguanosine",

author = "Kung, {Pei Pei} and Jones, {Roger A.}",

note = "Funding Information: Acknowledgement. This work was supported by grants from the National Instrtutes of Health (GM31483) and the Busch Memorial Fund, and an American Cancer SocretyF aculty ResearchA ward to R.A.J.",

year = "1991",

month = aug,

day = "5",

doi = "10.1016/0040-4039(91)80589-X",

language = "English (US)",

volume = "32",

pages = "3919--3922",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "32",

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TY - JOUR

T1 - One-Flask Syntheses of 6-Thioguanosine and 2′-Deoxy-6-Thioguanosine

AU - Kung, Pei Pei

AU - Jones, Roger A.

N1 - Funding Information: Acknowledgement. This work was supported by grants from the National Instrtutes of Health (GM31483) and the Busch Memorial Fund, and an American Cancer SocretyF aculty ResearchA ward to R.A.J.

PY - 1991/8/5

Y1 - 1991/8/5

N2 - We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2′-deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.

AB - We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2′-deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.

KW - 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine

KW - 2′-deoxy-6-thioguanosine

KW - 6-Thioguanosine

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U2 - 10.1016/0040-4039(91)80589-X

DO - 10.1016/0040-4039(91)80589-X

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AN - SCOPUS:0025779182

SN - 0040-4039

VL - 32

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EP - 3922

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 32

ER -

One-Flask Syntheses of 6-Thioguanosine and 2′-Deoxy-6-Thioguanosine

Abstract

All Science Journal Classification (ASJC) codes

Keywords

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