(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

Base Information

Chemical Name:(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol
CAS No.:691371-62-7
Molecular Formula:C₁₉H₂₅ClN₄O₅
Molecular Weight:424.884
Hs Code.:

Synonyms:(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

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Chemical Property of (1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

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Technology Process of (1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

There total 9 articles about (1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol 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%

: 691371-61-6
(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis[(trityloxy)methyl]-2-(benzyloxy)cyclohexane-1,3-diol

: 691371-62-7
(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 0.25h;
DOI:10.1135/cccc20040435

Reference yield:

: 360562-15-8
(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol

: 691371-62-7
(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 77 percent / pyridine / 1 h / 100 °C

2.1: 90 percent / thionyl chloride; Et₃N / diethyl ether / 4 h / -75 - -20 °C

3.1: pyridine / 20 °C

4.1: 4.95 g / aq. potassium periodate; RuCl₃ / CCl₄; acetonitrile / 1 h / 0 - 20 °C

5.1: LiN₃ / dimethylformamide / 1.5 h / 60 °C

5.2: 68 percent / aq. H₂SO₄ / tetrahydrofuran / 20 °C

6.1: 61 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Heating

7.1: 68 percent / Et₃N / ethanol / 96 h / 100 °C

8.1: 85 percent / aq. CF₃COOH / 0.25 h / 20 °C

With pyridine; ruthenium trichloride; lithium aluminium tetrahydride; thionyl chloride; lithium azide; potassium metaperiodate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1135/cccc20040435

Reference yield:

: 691371-40-1
(1R,2R,3R,4S)-3-(benzyloxy)-5,5-bis[(trityloxy)methyl]cyclohexane-1,2,4-triol

: 691371-62-7
(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 90 percent / thionyl chloride; Et₃N / diethyl ether / 4 h / -75 - -20 °C

2.1: pyridine / 20 °C

3.1: 4.95 g / aq. potassium periodate; RuCl₃ / CCl₄; acetonitrile / 1 h / 0 - 20 °C

4.1: LiN₃ / dimethylformamide / 1.5 h / 60 °C

4.2: 68 percent / aq. H₂SO₄ / tetrahydrofuran / 20 °C

5.1: 61 percent / LiAlH₄ / tetrahydrofuran / 2.5 h / Heating

6.1: 68 percent / Et₃N / ethanol / 96 h / 100 °C

7.1: 85 percent / aq. CF₃COOH / 0.25 h / 20 °C

With pyridine; ruthenium trichloride; lithium aluminium tetrahydride; thionyl chloride; lithium azide; potassium metaperiodate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1135/cccc20040435