1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

Base Information

Chemical Name:1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine
CAS No.:1338463-79-8
Molecular Formula:C₃₂H₃₄N₂O₁₄S₂
Molecular Weight:734.759
Hs Code.:

Synonyms:1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

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Chemical Property of 1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

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Technology Process of 1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

There total 5 articles about 1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-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:

: 1338463-76-5
1,2,4,6-tetra-O-acetyl-3-O-benzyl-5-C-(hydroxymethyl)-β-D-glucopyranose

: 1338463-79-8
1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: 0 °C / Reflux

3.1: 20 % Pd(OH)2/C; hydrogen / ethyl acetate / 14 h / 20 °C

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

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; 20 % Pd(OH)2/C; hydrogen; triethylamine; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/ol2025229

Reference yield:

: C₂₂H₂₆O₁₁

: 1338463-79-8
1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

Guidance literature:: Multi-step reaction with 5 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

With pyridine; dmap; sodium tetrahydroborate; N,O-bis-(trimethylsilyl)-acetamide; 20 % Pd(OH)2/C; hydrogen; triethylamine; In ethanol; dichloromethane; ethyl acetate; acetonitrile;
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

: 1338463-79-8
1-{2,4,6-tri-O-acetyl-3-O-(phenoxythiocarbonyl)-5-C-(tosyloxymethyl)-β-D-glucopyranosyl}thymine

Guidance literature:: Multi-step reaction with 3 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

With dmap; N,O-bis-(trimethylsilyl)-acetamide; 20 % Pd(OH)2/C; hydrogen; triethylamine; In dichloromethane; ethyl acetate; acetonitrile;
DOI:10.1021/ol2025229