N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Base Information

Chemical Name:N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine
CAS No.:368870-28-4
Molecular Formula:C₃₄H₄₀N₅O₈PS₂
Molecular Weight:741.826
Hs Code.:

Synonyms:N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

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Chemical Property of N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

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Technology Process of N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

There total 7 articles about N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine 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:

: 132342-52-0
((3aR,4R,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol

: 368870-28-4
N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / K₂CO₃ / methanol / 4 h / 20 °C

2.1: 71 percent / pyridine / 1.5 h / 20 °C

3.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

4.1: 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine; cyclohexylammonium / 1 h / 20 °C

4.2: 66 percent / pyridine / 1 h / 20 °C

5.1: 77 percent / 80percent aq. AcOH / 6 h / 20 °C

With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; cyclohexyl-ammonium cation; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; In tetrahydrofuran; methanol;
DOI:10.1021/ja010756d

Reference yield:

: 368870-20-6
5-[(methoxymethylene)amino]-1-[5-O-(tert-butyldimethylsilyl)-2,3-O-(isopropylidene)-β-D-ribofuranosyl]imidazole-4-nitrile

: 368870-28-4
N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 83 percent / K₂CO₃ / methanol / 4 h / 20 °C

2.1: 71 percent / pyridine / 1.5 h / 20 °C

3.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

4.1: 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine; cyclohexylammonium / 1 h / 20 °C

4.2: 66 percent / pyridine / 1 h / 20 °C

5.1: 77 percent / 80percent aq. AcOH / 6 h / 20 °C

With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; cyclohexyl-ammonium cation; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; In tetrahydrofuran; methanol;
DOI:10.1021/ja010756d

Reference yield:

: 197437-81-3
N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine

: 368870-28-4
N-1-[(1R,2S,3R,4R)-2,3-(isopropylidenedioxy)-4-(hydroxymethyl)cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 71 percent / pyridine / 1.5 h / 20 °C

2.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

3.1: 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine; cyclohexylammonium / 1 h / 20 °C

3.2: 66 percent / pyridine / 1 h / 20 °C

4.1: 77 percent / 80percent aq. AcOH / 6 h / 20 °C

With pyridine; 2,4,6-triisopropylphenylsulfonyl chloride; cyclohexyl-ammonium cation; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;
DOI:10.1021/ja010756d