(2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol
CAS No.:1459835-09-6
Molecular Formula:C₁₅H₂₁N₃O₃
Molecular Weight:291.35
Hs Code.:

Synonyms:(2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

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Chemical Property of (2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

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Technology Process of (2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

There total 11 articles about (2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-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: 94.0%

: 1459835-08-5
(2S,3R,5R,6S)-6-((benzyloxy)methyl)tetrahydro-2-(iodomethyl)-5-methyl-2H-pyran-3-ol

: 1459835-09-6
(2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 12h; Inert atmosphere;
DOI:10.1039/c3ob41088a

Reference yield:

: 1459834-83-3
C₁₄H₁₉NO₄

: 1459835-09-6
(2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: Noyori's catalyst; potassium carbonate / isopropyl alcohol; dichloromethane / 24 h / 55 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / Inert atmosphere

4.1: dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: lithium borohydride / tetrahydrofuran; methanol / 12 h / 0 - 20 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; lithium chloride; sodium persulfate / acetonitrile; water / 5 h / 10 °C / Inert atmosphere

7.2: 0.25 h / 0 °C / Inert atmosphere

7.3: 1 h / 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran / 3 h / -20 - 0 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

10.1: N-iodo-succinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

11.1: sodium azide / N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere

With 1H-imidazole; sodium persulfate; N-iodo-succinimide; lithium borohydride; Noyori's catalyst; n-butyllithium; sodium azide; (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; 6.1: |Dess-Martin Oxidation;
DOI:10.1039/c3ob41088a

Reference yield:

: 162255-09-6
<2S,3S>-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-4-(phenylmethoxy)butanal

: 1459835-09-6
(2R,3R,5R,6S)-2-(azidomethyl)-6-(benzyloxymethyl)-5-methyltetrahydro-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; methanol / 12 h / 0 - 20 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

4.1: (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; lithium chloride; sodium persulfate / acetonitrile; water / 5 h / 10 °C / Inert atmosphere

4.2: 0.25 h / 0 °C / Inert atmosphere

4.3: 1 h / 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran / 3 h / -20 - 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.1: N-iodo-succinimide / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

8.1: sodium azide / N,N-dimethyl-formamide / 12 h / 50 °C / Inert atmosphere

With sodium persulfate; N-iodo-succinimide; lithium borohydride; n-butyllithium; sodium azide; (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; tetrabutyl ammonium fluoride; Dess-Martin periodane; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: |Dess-Martin Oxidation;
DOI:10.1039/c3ob41088a