8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

Base Information

Chemical Name:8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine
CAS No.:239080-26-3
Molecular Formula:C₄₈H₅₉BrN₄O₉Si
Molecular Weight:944.007
Hs Code.:

8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

Synonyms:8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

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Chemical Property of 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

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Technology Process of 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

There total 12 articles about 8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine 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: 98.0%

: 239080-25-2
C₅₄H₆₄BrN₇O₁₃Si

: 239080-26-3
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃;
DOI:10.1016/S0040-4039(99)00977-6

Reference yield: 98.0%

: 239080-25-2
2-bromo-5-[[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]aminomethyleneamino]-1-[5-O-(monomethoxytrityl)-2,3-O-(isopropylidene)-β-D-ribofuranosyl]imidazole-4-(N-2,4-dinitrophenyl)carboxamide

: 239080-26-3
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 50 ℃; for 2.5h;
DOI:10.1021/jo0000877

Reference yield:

: 239080-20-7
5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

: 239080-26-3
8-bromo-N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-[[(tert-butyldimethylsilyl)oxy]methyl]cyclopentyl]-5'-O-(monomethoxytrityl)-2',3'-O-isopropylideneinosine

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / K₂CO₃ / dimethylformamide / 2.5 h / 80 °C

2: 74 percent / dimethylformamide / 21 h / 50 °C

3: 87 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

4: 88 percent / N-bromoacetamide / tetrahydrofuran / 0.5 h / -10 °C

5: 98 percent / K₂CO₃ / dimethylformamide / 2.5 h / 50 °C

With 1H-imidazole; potassium carbonate; N-bromoacetamide; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Substitution / 2: Ring cleavage / 3: silylation / 4: Bromination / 5: Cyclization;
DOI:10.1021/jo0000877