(1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine

Base Information

• Chemical Name: (1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine
• CAS No.: 660410-79-7
• Molecular Formula: C₂₅H₂₃N₅O₅
• Molecular Weight: 473.488

Synonyms:(1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine

Chemical Property of (1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine

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Technology Process of (1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine

There total 5 articles about (1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine 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:

(3aS,5R,6R,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3a-phenyl-hexahydro-furo[3,2-b]furan-2,6-diol → (1'S,3'R,4'R,5'R,7'R)-N6-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine (660410-79-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / pyridine / 39 h / 20 °C

2: 15 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 4 h / 50 °C

3: TBAF / tetrahydrofuran / 20 °C

4: NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

With pyridine; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ja037211z

Reference yield:

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane (389633-40-3) → (1'S,3'R,4'R,5'R,7'R)-N6-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine (660410-79-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 15 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 4 h / 50 °C

2: TBAF / tetrahydrofuran / 20 °C

3: NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ja037211z

Reference yield:

[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetaldehyde → (1'S,3'R,4'R,5'R,7'R)-N6-benzoyl-9-{4'-hydroxy-3'-hydroxymethyl-1'-phenyl-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine (660410-79-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 269 mg / aq. H₂SO₄ / tetrahydrofuran / 6 h / 60 °C

2: 90 percent / pyridine / 39 h / 20 °C

3: 15 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 4 h / 50 °C

4: TBAF / tetrahydrofuran / 20 °C

5: NaOH / tetrahydrofuran; methanol / 1 h / 0 °C

With pyridine; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1021/ja037211z

upstream raw materials:

(1R,3R,4R,5R,7RS)-1-phenyl-3-(tert-butyldiphenylsilyloxymethyl)-4,7-diacetoxy-2,6-dioxabicylco[3.3.0]octane

(1'S,3'R,4'R,5'R,7'R)-N⁶-benzoyl-9-{4'-acetoxy-1'-phenyl-3'-(tert-butyldiphenylsilyloxymethyl)-2',6'-dioxabicyclo[3.3.0]oct-7'-yl}adenine

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