1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

Base Information

Chemical Name:1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine
CAS No.:861231-14-3
Molecular Formula:C₃₆H₄₈N₄O₈Si
Molecular Weight:692.885
Hs Code.:

Synonyms:1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

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Chemical Property of 1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

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Technology Process of 1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

There total 12 articles about 1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-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: 86.0%

: 861231-13-2
1-[3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 861231-14-3
1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 36 ℃; for 12h;
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

: 861231-14-3
1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

Guidance literature:: Multi-step reaction with 12 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: 90 percent / NH₃ / methanol / 24 h / 20 °C

6.1: pyridine; triflic anhydride / CH₂Cl₂ / 12 h / -30 - 20 °C

6.2: 93 percent / tetrahydrofuran / 12 h / 20 °C

7.1: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

8.1: 87 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

9.1: aq. trifluoroacetic acid / 3 h / 20 °C

9.2: 93 percent / pyridine / 12 h / 20 °C

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

10.2: 76 percent / TMS-triflate / acetonitrile / 3 h / Heating

11.1: 57 percent / NH₃ / methanol / 1 h / 20 °C

12.1: 86 percent / DMAP; imidazole / dimethylformamide / 12 h / 36 °C

With pyridine; 1H-imidazole; dmap; N,O-bis-(trimethylsilyl)-acetamide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; ammonia; ammonium formate; triethylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5.1: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023

Reference yield:

: 861231-05-2
1,2-O-isopropylidene-4-C-(N-methylpiperazinyl)methyl-α-D-xylofuranose

: 861231-14-3
1-[2-O-tert-butyldimethylsilyl-3,5-di-O-benzoyl-4-C-(N-methylpiperazinyl)methyl-β-D-xylofuranosyl]thymine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / pyridine / CH₂Cl₂ / 12 h / 20 °C

2.1: aq. trifluoroacetic acid / 3 h / 20 °C

2.2: 93 percent / pyridine / 12 h / 20 °C

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

3.2: 76 percent / TMS-triflate / acetonitrile / 3 h / Heating

4.1: 57 percent / NH₃ / methanol / 1 h / 20 °C

5.1: 86 percent / DMAP; imidazole / dimethylformamide / 12 h / 36 °C

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