1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

Base Information

Chemical Name:1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine
CAS No.:861230-93-5
Molecular Formula:C₅₂H₅₈N₂O₉Si₂
Molecular Weight:911.212
Hs Code.:

Synonyms:1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

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Chemical Property of 1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

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Technology Process of 1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

There total 6 articles about 1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]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: 91.0%

: 861230-92-4
1,2-di-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-α,β-D-xylofuranose

: 65-71-4,28806-14-6,691841-57-3
thymin

: 861230-93-5
1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

Guidance literature:: 1,2-di-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-α,β-D-xylofuranose; thymin; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; for 1h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 12h; Heating;
DOI:10.1002/ejoc.200500023

Reference yield:

: 72261-44-0
1,2-O-isopropylidene-3-O-benzyl-4-C-(hydroxymethyl)-β-L-threo-pento-1,4-furanose

: 861230-93-5
1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 89 percent / ammonium formate / Pd(OH)2/C / methanol / 16 h / Heating

2.1: 93 percent / triethylamine / CH₂Cl₂ / 36 h / 20 °C

3.1: 86 percent / pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

4.1: 93 percent / DMAP; imidazole / dimethylformamide / 12 h / 20 °C

5.1: 87 percent / H₂SO₄; acetic acid / 4 h / 20 °C

6.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

6.2: 91 percent / TMS-triflate / acetonitrile / 12 h / Heating

With pyridine; 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonium formate; acetic acid; triethylamine; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200500023

Reference yield:

: 861230-89-9
5-O-(tert-butyldiphenylsilyl)-4-C-(hydroxymethyl)-1,2-O-isopropylidene-α-D-xylofuranose

: 861230-93-5
1-[2-O-acetyl-4-C-(benzoyloxymethyl)-3,5-di-O-(tert-butyldiphenylsilyl)-β-D-xylofuranosyl]thymine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / pyridine / CH₂Cl₂ / 12 h / 0 - 20 °C

2.1: 93 percent / DMAP; imidazole / dimethylformamide / 12 h / 20 °C

3.1: 87 percent / H₂SO₄; acetic acid / 4 h / 20 °C

4.1: N,O-bis(trimethylsilyl)acetamide / acetonitrile / 1 h / Heating

4.2: 91 percent / TMS-triflate / acetonitrile / 12 h / Heating

With pyridine; 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200500023