(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane
CAS No.:1092803-44-5
Molecular Formula:C₃₉H₄₀N₂O₅Si
Molecular Weight:644.842
Hs Code.:

Synonyms:(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

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Technology Process of (1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

There total 13 articles about (1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane 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:

: 1092803-43-4
C₄₇H₄₆N₂O₇SSi

: 1092803-44-5
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Guidance literature:: C₄₇H₄₆N₂O₇SSi; With tri-n-butyl-tin hydride; In toluene; for 0.5h; Reflux;

With 2,2'-azobis(isobutyronitrile); In toluene; for 3.5h; Reflux;

Reference yield:

: 1092803-42-3
C₃₉H₄₀N₂O₆Si

: 1092803-44-5
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Guidance literature:: C₃₉H₄₀N₂O₆Si; With dmap; In acetonitrile; at 0 ℃; for 1h;

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 4h; Reflux;
DOI:10.1021/ja105875e

Reference yield:

: 956485-06-6
3-O-(2-naphthylmethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 1092803-44-5
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 17 steps

1.1: water; acetic acid / 16 h / 20 °C

2.1: sodium periodate / 1,4-dioxane; water / 1.67 h

3.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice

4.1: triethylamine / dichloromethane; methanol / 18 h / 0 - 20 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

6.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C

6.2: 16.33 h / -78 - 20 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

7.2: 4 h / 50 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

8.2: 0.5 h

9.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

9.2: 2 h / -78 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

11.1: tetrahydrofuran; hexanes / 0.5 h / -78 °C

12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

13.1: sulfuric acid / 0.25 h / 20 °C

14.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / Cooling with ice; Reflux

15.1: ammonia / methanol / 16 h / 20 °C

16.1: dmap / acetonitrile / 1 h / 0 °C

17.1: tri-n-butyl-tin hydride / toluene / 0.5 h / Reflux

17.2: 3.5 h / Reflux

With dmap; sodium periodate; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; water; tri-n-butyl-tin hydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 14.1: Vorbrugen reaction;