1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

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Chemical Name:1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine
CAS No.:1338463-85-6
Molecular Formula:C₃₃H₃₄N₂O₈
Molecular Weight:586.642
Hs Code.:

Synonyms:1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

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Chemical Property of 1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

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Technology Process of 1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

There total 11 articles about 1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

: 1338463-84-5
1-(3-deoxy-2-O,5-C-methylene-β-D-glucopyranosyl)thymine

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 1338463-85-6
1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

Guidance literature:: With pyridine; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/ol2025229

Reference yield:

: C₂₂H₂₆O₁₁

: 1338463-85-6
1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium tetrahydroborate / ethanol; dichloromethane / 1 h / -78 - 20 °C / Inert atmosphere

2.1: pyridine / 18 h / 20 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Reflux

3.2: 0 °C / Reflux

4.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 14 h / 20 °C

5.1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

6.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / toluene / 4 h / 80 °C / Inert atmosphere

7.1: potassium carbonate / methanol / 0.25 h / 20 °C

8.1: (1S)-10-camphorsulfonic acid / acetone / 26 h / 20 °C / Inert atmosphere

9.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 10 h / 60 °C / Inert atmosphere

10.1: acetic acid / water / 13 h / 20 °C

11.1: pyridine / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; 20 % Pd(OH)2/C; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; In methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol2025229

Reference yield:

: 1338463-77-6
1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(tosyloxymethyl)-β-D-glucopyranose

: 1338463-85-6
1-{3-deoxy-6-O-(4,4'-dimethoxytrityl)-2-O,5-C-methylene-β-D-glucopyranosyl}thymine

Guidance literature:: Multi-step reaction with 9 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Reflux

1.2: 0 °C / Reflux

2.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 14 h / 20 °C

3.1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / toluene / 4 h / 80 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 0.25 h / 20 °C

6.1: (1S)-10-camphorsulfonic acid / acetone / 26 h / 20 °C / Inert atmosphere

7.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 10 h / 60 °C / Inert atmosphere

8.1: acetic acid / water / 13 h / 20 °C

9.1: pyridine / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; 20 % Pd(OH)2/C; (1S)-10-camphorsulfonic acid; hydrogen; sodium hydride; potassium carbonate; acetic acid; triethylamine; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil;
DOI:10.1021/ol2025229