The preparation of diribonucleoside monophosphates containing 4‐thiouridine via the phosphotriester approach

J. H. van Boom; P. M.J. Burgers; J. den Hartog; G. van der Marel

doi:10.1002/recl.19760950507

The preparation of diribonucleoside monophosphates containing 4‐thiouridine via the phosphotriester approach

J. H. van Boom
, P. M.J. Burgers
, J. den Hartog
, G. van der Marel

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

11 Scopus citations

Abstract

A new procedure for the synthesis of 2′‐ketals of 4‐thiouridine (1c), N⁴‐methylcytidine (2a) and N⁴,N⁴‐dimethylcytidine (2b), starting from the. easily accessible 3′,5′‐di‐O‐acetyl‐2′‐O‐(methoxytetrahydropyranyl)uridine (1b), has been devised. Modified dinucleoside monophosphates i⁶Aps⁴U (7a) and s⁴UpU (7b) have been prepared, in satisfactory yields, by appropriate internucleotide bond formation between (1c) and the corresponding 5′‐ester (1d) with 2′,5′‐di^eO‐(methoxytetrahydropyranyl)‐N⁶‐(Δ²‐isopentenyl)adenosine (3) and 2′,3′‐O‐methoxymethylideneuridine (4), respectively.

Original language	English
Pages (from-to)	108-112
Number of pages	5
Journal	Recueil des Travaux Chimiques des Pays‐Bas
Volume	95
Issue number	5
DOIs	https://doi.org/10.1002/recl.19760950507
State	Published - 1976

Access to Document

10.1002/recl.19760950507

Cite this

@article{b5123a95b5a84718bfc1463c21e1186e,

title = "The preparation of diribonucleoside monophosphates containing 4‐thiouridine via the phosphotriester approach",

abstract = "A new procedure for the synthesis of 2′‐ketals of 4‐thiouridine (1c), N4‐methylcytidine (2a) and N4,N4‐dimethylcytidine (2b), starting from the. easily accessible 3′,5′‐di‐O‐acetyl‐2′‐O‐(methoxytetrahydropyranyl)uridine (1b), has been devised. Modified dinucleoside monophosphates i6Aps4U (7a) and s4UpU (7b) have been prepared, in satisfactory yields, by appropriate internucleotide bond formation between (1c) and the corresponding 5′‐ester (1d) with 2′,5′‐dieO‐(methoxytetrahydropyranyl)‐N6‐(Δ2‐isopentenyl)adenosine (3) and 2′,3′‐O‐methoxymethylideneuridine (4), respectively.",

author = "\{van Boom\}, \{J. H.\} and Burgers, \{P. M.J.\} and \{den Hartog\}, J. and \{van der Marel\}, G.",

year = "1976",

doi = "10.1002/recl.19760950507",

language = "English",

volume = "95",

pages = "108--112",

journal = "Recueil des Travaux Chimiques des Pays‐Bas",

issn = "0165-0513",

number = "5",

}

TY - JOUR

T1 - The preparation of diribonucleoside monophosphates containing 4‐thiouridine via the phosphotriester approach

AU - van Boom, J. H.

AU - Burgers, P. M.J.

AU - den Hartog, J.

AU - van der Marel, G.

PY - 1976

Y1 - 1976

N2 - A new procedure for the synthesis of 2′‐ketals of 4‐thiouridine (1c), N4‐methylcytidine (2a) and N4,N4‐dimethylcytidine (2b), starting from the. easily accessible 3′,5′‐di‐O‐acetyl‐2′‐O‐(methoxytetrahydropyranyl)uridine (1b), has been devised. Modified dinucleoside monophosphates i6Aps4U (7a) and s4UpU (7b) have been prepared, in satisfactory yields, by appropriate internucleotide bond formation between (1c) and the corresponding 5′‐ester (1d) with 2′,5′‐dieO‐(methoxytetrahydropyranyl)‐N6‐(Δ2‐isopentenyl)adenosine (3) and 2′,3′‐O‐methoxymethylideneuridine (4), respectively.

AB - A new procedure for the synthesis of 2′‐ketals of 4‐thiouridine (1c), N4‐methylcytidine (2a) and N4,N4‐dimethylcytidine (2b), starting from the. easily accessible 3′,5′‐di‐O‐acetyl‐2′‐O‐(methoxytetrahydropyranyl)uridine (1b), has been devised. Modified dinucleoside monophosphates i6Aps4U (7a) and s4UpU (7b) have been prepared, in satisfactory yields, by appropriate internucleotide bond formation between (1c) and the corresponding 5′‐ester (1d) with 2′,5′‐dieO‐(methoxytetrahydropyranyl)‐N6‐(Δ2‐isopentenyl)adenosine (3) and 2′,3′‐O‐methoxymethylideneuridine (4), respectively.

UR - https://www.scopus.com/pages/publications/84983933789

U2 - 10.1002/recl.19760950507

DO - 10.1002/recl.19760950507

M3 - Article

AN - SCOPUS:84983933789

SN - 0165-0513

VL - 95

SP - 108

EP - 112

JO - Recueil des Travaux Chimiques des Pays‐Bas

JF - Recueil des Travaux Chimiques des Pays‐Bas

IS - 5

ER -

The preparation of diribonucleoside monophosphates containing 4‐thiouridine via the phosphotriester approach

Abstract

Access to Document

Other files and links

Fingerprint

Cite this