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360139

Sigma-Aldrich

5′-O-(4,4′-Dimethoxytrityl)thymidine

98%

Synonym(s):

DMT-T

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About This Item

Empirical Formula (Hill Notation):
C31H32N2O7
CAS Number:
40615-39-2
Molecular Weight:
544.59
Beilstein:
599297
EC Number:
255-003-1
MDL number:
MFCD00010113
UNSPSC Code:
12352100
PubChem Substance ID:
24862149
NACRES:
NA.22

Assay

98%

mp

114-116 °C (subl.) (lit.)

storage temp.

2-8°C

SMILES string

COc1ccc(cc1)C(OC[C@H]2O[C@H](C[C@@H]2O)N3C=C(C)C(=O)NC3=O)(c4ccccc4)c5ccc(OC)cc5

InChI

1S/C31H32N2O7/c1-20-18-33(30(36)32-29(20)35)28-17-26(34)27(40-28)19-39-31(21-7-5-4-6-8-21,22-9-13-24(37-2)14-10-22)23-11-15-25(38-3)16-12-23/h4-16,18,26-28,34H,17,19H2,1-3H3,(H,32,35,36)/t26-,27+,28+/m0/s1

InChI key

UBTJZUKVKGZHAD-UPRLRBBYSA-N

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General description

5′-O-(4,4′-Dimethoxytrityl)thymidine is a pyrimidine.

Application

5′-O-(4,4′-Dimethoxytrityl)thymidine may be used in the stereoselective synthesis of 3′-deoxy-3′-threo-hydroxymethyl nucleoside, which can be subsequently incorporated into oligodeoxynucleotides. It may be used as research tool for antiviral and anticancer studies.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Oligodeoxynucleotide analogues containing 3'-deoxy-3'-C- threo-hydroxymethylthymidine: Synthesis, hybridization properties and enzymatic stability.
Svendsen ML, et al.
Tetrahedron, 49(48), 11341-11352 (1993)
A Elmblad et al.
Nucleic acids research, 10(10), 3291-3301 (1982-05-25)
A method for the synthesis of mixed dimers, trimers and oligonucleotides on a solid support using monomeric protected nucleoside phosphochloridites (1a-d) has been developed and the different nucleoside reagents, and the results show that yields of different oligomers in a
Tamara I Prykota et al.
Nucleosides, nucleotides & nucleic acids, 30(7-8), 544-551 (2011-09-06)
A new labeling technique attaching a fluorescent pteridine derivative (3, 5) via a linker onto the 3'-OH group of 5'-O-dimethoxytritylthymidine (7) was developed to lead to the conjugates 8 and 11. After detritylation to give 9 and 12, the final
A Guzaev et al.
Bioorganic & medicinal chemistry letters, 8(9), 1123-1126 (1999-01-01)
A novel solid-phase synthesis of 5'-radiolabeled oligonucleotides is described. The labeling reaction is carried out by the phosphoramidite method with the aid of [4,6-di-14C]-5'-dimethoxytritylthymidine building block 1. The feasibility of the method is demonstrated by preparation of 3'-phosphorylated dodecathymidylate phosphorothioate
K Miyoshi et al.
Nucleic acids research, 8(22), 5473-5489 (1980-11-25)
Synthesis of two oligothymidylic acids, tridecamer and nonadecamer, is described by a rapid and simple solid-phase method on two kinds of polyacrylamide supports derivatized from commercially available Enzacryl Gel K-2. The syntheses were performed by the phosphotriester method using di-
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