(1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane
CAS No.:1529813-98-6
Molecular Formula:C₃₀H₄₆N₂O₈Si₂
Molecular Weight:618.875
Hs Code.:

Synonyms:(1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

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Chemical Property of (1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

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Technology Process of (1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

There total 4 articles about (1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-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: 85.0%

: (1R,5R,6R,8S)-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-4-hydroxy-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

: 98-88-4
benzoyl chloride

: 1529813-98-6
(1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

Guidance literature:: With pyridine; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2013.12.013

Reference yield:

: 913972-64-2
2'-deoxy-2'-C-allyl-4'-C-hydroxymethyl-3',5'-di-O-(tert-butyldimethylsilyl)uridine

: 1529813-98-6
(1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

1: rhodium(III) trichloride hydrate; potassium carbonate / ethanol / 3 h / 80 °C / Inert atmosphere; Microwave irradiation

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide; water / acetone; tert-butyl alcohol / 17 h / 20 °C

3: sodium periodate / water; 1,4-dioxane / 6 h / 20 °C

4: pyridine / 1 h / 20 °C / Inert atmosphere

With pyridine; sodium periodate; osmium(VIII) oxide; rhodium(III) trichloride hydrate; water; potassium carbonate; 4-methylmorpholine N-oxide; In 1,4-dioxane; ethanol; water; acetone; tert-butyl alcohol;
DOI:10.1016/j.tet.2013.12.013

Reference yield:

: 1529814-13-8
C₂₅H₄₈N₂O₈Si₂

: 1529813-98-6
(1R,5R,6R,8S)-4-benzoyloxy-8-(tert-butyldimethylsilyloxy)-1-(tert-butyldimethylsilyloxymethyl)-6-(uracil-1-yl)-3,7-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 2 steps

1: sodium periodate / water; 1,4-dioxane / 6 h / 20 °C

2: pyridine / 1 h / 20 °C / Inert atmosphere

With pyridine; sodium periodate; In 1,4-dioxane; water;
DOI:10.1016/j.tet.2013.12.013