N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Base Information

Chemical Name:N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine
CAS No.:1356151-96-6
Molecular Formula:C₄₀H₄₇BrN₄O₁₂Si
Molecular Weight:883.822
Hs Code.:

Synonyms:N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Chemical Property:

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Technology Process of N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

There total 3 articles about N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine 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: 90.0%

: 1256503-22-6
5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

: 13035-61-5
1,2,3,5-tetraacetylribose

: 1356151-96-6
N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Guidance literature:: 5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.5h;

1,2,3,5-tetraacetylribose; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 20 ℃; stereoselective reaction;
DOI:10.1021/jo202319f

Reference yield:

: 362-75-4
2',3'-isopropylidene adenosine

: 1356151-96-6
N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Guidance literature:: Multi-step reaction with 4 steps

1.1: disodium hydrogenphosphate; bromine / 1,4-dioxane; water / 16 h / Darkness

2.1: sodium nitrite / water; acetic acid / 16 h

3.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

4.2: -78 - 20 °C

With 1H-imidazole; disodium hydrogenphosphate; bromine; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo202319f

Reference yield:

: 13089-45-7
8-bromo-2',3'-O-isopropylene adenosine

: 1356151-96-6
N1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-5'-O-(tert-butyldiphenylsilyl)-2',3'-O-isopropylidene-8-bromoinosine

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium nitrite / water; acetic acid / 16 h

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h

3.2: -78 - 20 °C

With 1H-imidazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium nitrite; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo202319f