(-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

Base Information

Chemical Name:(-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol
CAS No.:1339886-50-8
Molecular Formula:C₁₈H₁₇IN₈O
Molecular Weight:488.29
Hs Code.:

Synonyms:(-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

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Chemical Property of (-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

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Technology Process of (-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

There total 9 articles about (-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol 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: 76.0%

: 1339886-47-3
(-)-(1R,2R,3S,4R,5S)-2-azido-4-(6-chloro-purin-9-yl)-bicyclo[3.1.0]hexan-3-ol

: 696-40-2
3-iodobenzylamine

: 1339886-50-8
(-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: In ethanol; at 20 ℃;
DOI:10.1039/c1ob05853c

Reference yield:

: 1078503-71-5
(3aR,3bR,4aS,5S,5aS)-2,2-dimethylhexahydrocyclopropa[3,4]-cyclopenta[1,2-d][1,3]dioxol-5-ol

: 1339886-50-8
(-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: pyridine / 3.5 h / 20 °C

2.1: trifluoroacetic acid / 20 °C

3.1: acetonitrile / 3.5 h / 0 °C

4.1: sodium azide / N,N-dimethyl-formamide / 3 h / 100 °C

5.1: sodium methylate / methanol / 2 h / 20 °C

6.1: thionyl chloride; triethylamine / dichloromethane / 0.17 h / 0 °C

7.1: sodium periodate; ruthenium(III) chloride trihydrate / tetrachloromethane; water; acetonitrile / 0.17 h / 20 °C

8.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran; mineral oil / 3 h / 80 °C

8.2: 4 h / 20 °C

8.3: 0 - 20 °C / pH 2

9.1: ethanol / 20 °C

With pyridine; sodium periodate; thionyl chloride; sodium azide; 18-crown-6 ether; ruthenium(III) chloride trihydrate; sodium methylate; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1039/c1ob05853c

Reference yield:

: 1339886-45-1
(-)-(1S,2S,3S,4R,5R)-4-azido-bicyclo[3.1.0]hexane-2,3-O-sulphite

: 1339886-50-8
(-)-(1R,2R,3S,4R,5S)-2-azido-4-[6-(3-iodo-benzylamino)-purin-9-yl]-bicyclo[3.1.0]hexan-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium periodate; ruthenium(III) chloride trihydrate / tetrachloromethane; water; acetonitrile / 0.17 h / 20 °C

2.1: 18-crown-6 ether; sodium hydride / tetrahydrofuran; mineral oil / 3 h / 80 °C

2.2: 4 h / 20 °C

2.3: 0 - 20 °C / pH 2

3.1: ethanol / 20 °C

With sodium periodate; 18-crown-6 ether; ruthenium(III) chloride trihydrate; sodium hydride; In tetrahydrofuran; tetrachloromethane; ethanol; water; acetonitrile; mineral oil;
DOI:10.1039/c1ob05853c