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

Base Information

Chemical Name:8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine
CAS No.:623547-32-0
Molecular Formula:C₅₄H₅₅ClN₅O₉PS₂
Molecular Weight:1048.62
Hs Code.:

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

Synonyms:8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

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Chemical Property of 8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

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Technology Process of 8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

There total 7 articles about 8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]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: 67.0%

: 23282-01-1
(S,S')-diphenylphosphorodithioate

: 623547-31-9
8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-2',3'-O-isopropylideneadenosine

: 623547-32-0
8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Guidance literature:: (S,S')-diphenylphosphorodithioate; With pyridine; Triphenylsilyl chloride; at 20 ℃; for 2h;

8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-2',3'-O-isopropylideneadenosine; With pyridine; at 20 ℃; for 2h;
DOI:10.1021/jm030227f

Reference yield:

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

: 623547-32-0
8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / K₂CO₃ / dimethylformamide / 20 h / 20 °C

2.1: 79 percent / pyridine / 1.5 h / 20 °C

3.1: 88 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

4.1: TPSCl; pyridine / 2 h / 20 °C

4.2: 67 percent / pyridine / 2 h / 20 °C

With pyridine; Triphenylsilyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jm030227f

Reference yield:

: 5-amino-1-[5'-O-(tert-butyldimethylsilyl)-2',3-Oisopropylidene-β-D-ribofuranosyl]-1H-imidazole-4-carbonitrile

: 623547-32-0
8-chloro-N-1-[(1R,2S,3R,4R)-2,3-isopropylidenedioxy-4-[(5-monomethoxytrityl)oxymethyl]cyclopentyl]-5'-O-[bis(phenylthio)phosphoryl]-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 84 percent / N-chlorosuccinimide / tetrahydrofuran / 10.5 h / 20 °C

2.1: 95 percent / TFA / 0.17 h / 50 °C

3.1: 89 percent / K₂CO₃ / dimethylformamide / 20 h / 20 °C

4.1: 79 percent / pyridine / 1.5 h / 20 °C

5.1: 88 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

6.1: TPSCl; pyridine / 2 h / 20 °C

6.2: 67 percent / pyridine / 2 h / 20 °C

With pyridine; N-chloro-succinimide; Triphenylsilyl chloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jm030227f