(1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane
CAS No.:361344-53-8
Molecular Formula:C₃₂H₃₂N₂O₈
Molecular Weight:572.615
Hs Code.:

Synonyms:(1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

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Chemical Property of (1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

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Technology Process of (1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

There total 11 articles about (1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane 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%

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 361344-52-7
(1S,5S,6S)-6-hydroxy-5-hydroxymethyl-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

: 361344-53-8
(1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

Guidance literature:: With pyridine; for 2.83333h;
DOI:10.1021/jo015664l

Reference yield:

: 175355-17-6
1-[3'-Deoxy-6'-O-(4,4'-dimethoxytrityl)-β-D-psicofuranosyl]uracil

: 361344-53-8
(1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran / 8 h / 20 °C

1.2: 85 percent / NaH / tetrahydrofuran / 15 h / 20 °C

2.1: 94 percent / aq. AcOH / CH₂Cl₂ / 1.5 h

3.1: Dess-Martin periodinane / CH₂Cl₂ / 0.67 h

4.1: 1.27 percent / aq. NaOH / dioxane; H₂O / 22 h

5.1: pyridine / 1.33 h / 0 °C

6.1: 252 mg / H₂ / Pd(OH)2C / CH₂Cl₂; ethanol / 7 h

7.1: 64 percent / aq. NaOH / dioxane / 22 h / 90 °C

8.1: dimethylformamide / 36 h / 120 °C

9.1: 145 mg / NaOMe / methanol / 1.5 h

10.1: 84 percent / BCl₃ / CH₂Cl₂; hexane / 7 h / -78 °C

11.1: 67 percent / pyridine / 2.83 h

With pyridine; sodium hydroxide; hydrogen; sodium methylate; boron trichloride; sodium hydride; Dess-Martin periodane; acetic acid; palladium hydroxide - carbon; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo015664l

Reference yield:

: (2S,3S,5S)-3-Benzyloxy-5-benzyloxymethyl-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carbaldehyde

: 361344-53-8
(1S,5R,6S)-5-(4,4'-dimethoxytrityloxymethyl)-6-hydroxy-1-(uracil-1-yl)-3,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 8 steps

1: 1.27 percent / aq. NaOH / dioxane; H₂O / 22 h

2: pyridine / 1.33 h / 0 °C

3: 252 mg / H₂ / Pd(OH)2C / CH₂Cl₂; ethanol / 7 h

4: 64 percent / aq. NaOH / dioxane / 22 h / 90 °C

5: dimethylformamide / 36 h / 120 °C

6: 145 mg / NaOMe / methanol / 1.5 h

7: 84 percent / BCl₃ / CH₂Cl₂; hexane / 7 h / -78 °C

8: 67 percent / pyridine / 2.83 h

With pyridine; sodium hydroxide; hydrogen; sodium methylate; boron trichloride; palladium hydroxide - carbon; In 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo015664l