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

Base Information

Chemical Name:{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4R,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate
CAS No.:1613144-90-3
Molecular Formula:C₄₃H₅₄O₁₀S₂Si
Molecular Weight:823.113
Hs Code.:

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

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

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

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

There total 9 articles about {(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4R,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate 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:

: 1613144-82-3
{(2R,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 501365-06-6
(R)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

: 1613144-89-0
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4S,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 1613144-90-3
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4R,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Guidance literature:: {(2R,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate; (R)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;

With sodium hydrogencarbonate; triethylamine; In dichloromethane; water; at 20 ℃; for 2h; pH=> 7; Overall yield = 55 %; Overall yield = 172 mg; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c4cc02702g

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1613144-89-0
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4S,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 1613144-90-3
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4R,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 118629-75-7
(S)-2-hydroxypent-4-en-1-yl 4-methylbenzenesulfonate

: 1613144-89-0
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4S,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

: 1613144-90-3
{(2S,4S,6S)-4-[(tert-butyldiphenylsilyl)oxy]-6-[((2S,4R,6R)-4-hydroxy-6-(tosyloxymethyl)tetrahydro-2H-pyran-2-yl)methyl]tetrahydro-2H-pyran-2-yl}methyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: 3 h / 20 °C / pH > 7 / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 16 h / 20 °C / Inert atmosphere

3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate; methanol / 16 h / 20 °C / 760.05 Torr

4.1: 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate / dichloromethane / 2 h / 20 °C / Molecular sieve; Inert atmosphere

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

5.2: 2 h / 20 °C / pH > 7 / Inert atmosphere

With 1H-imidazole; tetrapropylammonium perruthennate; palladium 10% on activated carbon; hydrogen; 4-methylmorpholine N-oxide; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;
DOI:10.1021/acs.joc.5b01323