((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane
• CAS No.: 1459835-21-2
• Molecular Formula: C₂₁H₃₅N₃O₃Si
• Molecular Weight: 405.613

Synonyms:((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Chemical Property of ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

There total 14 articles about ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane 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: 96.0%

((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol (1459835-20-1) → ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1459835-21-2)

Guidance literature:

With di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; triphenylphosphine; at 0 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c3ob41088a

Reference yield:

C14H19NO4 (1459834-83-3) → ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1459835-21-2)

Guidance literature:

Multi-step reaction with 14 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: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

12.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

13.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

13.2: Inert atmosphere

14.1: di-isopropyl azodicarboxylate; triphenylphosphine; diphenylphosphoranyl azide / 3 h / 0 °C / Inert atmosphere

With 1H-imidazole; sodium persulfate; N-iodo-succinimide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; Noyori's catalyst; n-butyllithium; di-isopropyl azodicarboxylate; (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; diphenylphosphoranyl azide; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; triphenylphosphine; 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:

<2S,3S>-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2-methyl-4-(phenylmethoxy)butanal (162255-09-6) → ((2R,3R,5R,6S)-2-(azidomethyl)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane (1459835-21-2)

Guidance literature:

Multi-step reaction with 11 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: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

9.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

10.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

10.2: Inert atmosphere

11.1: di-isopropyl azodicarboxylate; triphenylphosphine; diphenylphosphoranyl azide / 3 h / 0 °C / Inert atmosphere

With 1H-imidazole; sodium persulfate; N-iodo-succinimide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; di-isopropyl azodicarboxylate; (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; diphenylphosphoranyl azide; potassium tert-butylate; tetrabutyl ammonium fluoride; Dess-Martin periodane; triphenylphosphine; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: |Dess-Martin Oxidation;

DOI:10.1039/c3ob41088a

upstream raw materials:

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

<2S,3S>-3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>-N-methoxy>-N,2-dimethyl-4-phenylmethoxybutanamide

(4R,5S,E)-ethyl 6-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methylhex-2-enoate

(4R,5S)-6-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methylhexan-1-ol

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