bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

Base Information

Chemical Name:bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane
CAS No.:1613144-91-4
Molecular Formula:C₅₉H₇₂O₁₀S₂Si₂
Molecular Weight:1061.52
Hs Code.:

Synonyms:bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

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Chemical Property of bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

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Technology Process of bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

There total 4 articles about bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane 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%

: 1613144-83-4
{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2R,4R,6S)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1613144-91-4
bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1039/c4cc02702g

Reference yield:

: 70987-78-9,6746-81-2
(S)-Glycidyl tosylate

: 1613144-91-4
bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

Guidance literature:: Multi-step reaction with 3 steps

1.1: dilithium tetrachlorocuprate / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere

1.2: 4 h / -40 °C / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

With 1H-imidazole; dilithium tetrachlorocuprate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c4cc02702g

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1613144-91-4
bis{(2S,4R,6S)-4-[(tert-butyldiphenylsilyl)oxy]-2-(tosyloxymethyl)tetrahydro-2H-pyran-6-yl}methane

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

2.1: dilithium tetrachlorocuprate / tetrahydrofuran / 1 h / -40 °C / Inert atmosphere

2.2: 4 h / -40 °C / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 24 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; dilithium tetrachlorocuprate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1039/c4cc02702g