3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

Base Information

Chemical Name:3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose
CAS No.:861231-04-1
Molecular Formula:C₄₇H₅₉F₃N₂O₆Si₂
Molecular Weight:861.161
Hs Code.:

Synonyms:3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

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Chemical Property of 3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

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Technology Process of 3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

There total 7 articles about 3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose 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: 87.0%

: 861231-03-0
3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-piperazinylmethyl-α-D-xylofuranose

: 407-25-0
trifluoroacetic anhydride

: 861231-04-1
3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 4h;
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

: 861231-04-1
3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 7 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: 91 percent / tetrahydrofuran / 12 h / 20 °C

7.1: 87 percent / triethylamine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 1H-imidazole; dmap; trifluoromethylsulfonic anhydride; ammonia; ammonium formate; triethylamine; palladium dihydroxide; In methanol; dichloromethane; N,N-dimethyl-formamide; 5.1: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023

Reference yield:

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

: 861231-04-1
3,5-di-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-4-C-(N-trifluoroacetylpiperazinyl)methyl-α-D-xylofuranose

Guidance literature:: Multi-step reaction with 5 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: 90 percent / NH₃ / methanol / 24 h / 20 °C

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

4.2: 91 percent / tetrahydrofuran / 12 h / 20 °C

5.1: 87 percent / triethylamine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; 1H-imidazole; dmap; trifluoromethylsulfonic anhydride; ammonia; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide; 3.1: Zemplen O-debenzoylation;
DOI:10.1002/ejoc.200500023