((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

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Chemical Name:((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol
CAS No.:1459835-20-1
Molecular Formula:C₂₁H₃₆O₄Si
Molecular Weight:380.6
Hs Code.:

Synonyms:((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

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Chemical Property of ((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

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Technology Process of ((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

There total 13 articles about ((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol 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: 92.0%

: 1459835-19-8
((3R,5R,6S)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2-methylene-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

: 1459835-20-1
((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

Guidance literature:: ((3R,5R,6S)-6-((benzyloxy)methyl)tetrahydro-5-methyl-2-methylene-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;

With dihydrogen peroxide; potassium hydroxide; In tetrahydrofuran; water; Inert atmosphere;
DOI:10.1039/c3ob41088a

Reference yield:

: 1459834-83-3
C₁₄H₁₉NO₄

: 1459835-20-1
((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

Guidance literature:: Multi-step reaction with 13 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

With 1H-imidazole; sodium persulfate; N-iodo-succinimide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; Noyori's catalyst; n-butyllithium; (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; potassium tert-butylate; 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

: 1459835-20-1
((2S,3R,5R,6S)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-5-methyltetrahydro-2H-pyran-2-yl)methanol

Guidance literature:: Multi-step reaction with 10 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

With 1H-imidazole; sodium persulfate; N-iodo-succinimide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; (2S,5R)‐2‐(tert‐butyl)‐3,5‐dimethylimidazolidin‐4‐one trifluoroacetate; coppertrifluoroacetate hydrate; potassium tert-butylate; 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