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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

Quality Level

100

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBC6386
11314EJ
00528EJ
06731ME
02004CD

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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
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-
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
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