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

Base Information

Chemical Name:N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine
CAS No.:859147-59-4
Molecular Formula:C₃₁H₃₆N₅O₆PS₂
Molecular Weight:669.762
Hs Code.:

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

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

Chemical Property:

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

There total 10 articles about N-1-{(1S,4R)-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: 85.0%

: 859147-57-2
N-1-[(1S,4R)-4-{(monomethoxytrityl)oxymethyl}cyclopentyl]-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine

: 859147-59-4
N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine

Guidance literature:: With acetic acid; at 20 ℃; for 7h;
DOI:10.1021/ja050732x

Reference yield:

: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

: 859147-59-4
N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / H₂ / Pd-C / methanol / 5 h / 20 °C / atmospheric pressure

2.1: 100 percent / DMAP / acetonitrile / 1 h / 20 °C

3.1: 95 percent / NaBH₄ / methanol / 0.5 h / 0 °C

4.1: 100 percent / water / 18 h / Heating

5.1: 85 percent / K₂CO₃ / methanol / 14 h / 20 °C

6.1: 97 percent / pyridine / 4 h / 20 °C

7.1: 100 percent / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

8.1: 2,4,6-triisopropylbenzenesulfonyl chloride; pyridine / 1 h / 20 °C

8.2: 69 percent / pyridine / 1 h / 20 °C

9.1: 85 percent / aq. AcOH / 7 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; 2,4,6-triisopropylphenylsulfonyl chloride; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1021/ja050732x

Reference yield:

: 859147-51-6
N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine

: 859147-59-4
N-1-{(1S,4R)-4-(hydroxymethyl)cyclopentyl}-5'-O-{bis(phenylthio)phosphoryl}-2',3'-O-isopropylideneadenosine

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine

2: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran

3: TPSCl; pyridine

4: aq. AcOH

With pyridine; Triphenylsilyl chloride; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran;
DOI:10.1081/NCN-200060167