(2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

Base Information

Chemical Name:(2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol
CAS No.:1352832-11-1
Molecular Formula:C₂₇H₃₄O₈
Molecular Weight:486.562
Hs Code.:

Synonyms:(2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

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Chemical Property of (2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

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Technology Process of (2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

There total 12 articles about (2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol 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%

: 273944-69-7
(2S,4R,5R,6R,7R,8R,9R)-2,9-dibenzoyloxy-7-diethylisopropylsilyloxy-5-hydroxy-4-methoxy-6,8-dimethyldecan-3-one

: 1352832-11-1
(2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

Guidance literature:: With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2011.09.012

Reference yield:

: 273944-68-6
C₂₄H₃₅BO₄

: 1352832-11-1
(2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: diethyl ether / 18 h / -78 - -20 °C / Inert atmosphere

1.2: 1 h / 0 °C / pH 7 / aq. buffer

2.1: hydrogenchloride; water / tetrahydrofuran / 4 h / 20 °C

With hydrogenchloride; water; In tetrahydrofuran; diethyl ether; 1.1: Aldol reaction;
DOI:10.1016/j.tet.2011.09.012

Reference yield:

: 116652-75-6
(R)-1-(benzyloxy)-2-methylpentan-3-one

: 1352832-11-1
(2R,3R,4R,5R,6R)-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2,4-diol

Guidance literature:: Multi-step reaction with 8 steps

1.1: triethylamine / diethyl ether / 2 h / 0 °C / Inert atmosphere

2.1: diethyl ether / 11 h / -78 - -20 °C / Inert atmosphere

2.2: 1.5 h / 0 °C / pH 7 / aq. buffer

3.1: samarium diiodide / tetrahydrofuran / 2 h / -10 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

5.1: 10% Pd(OH)₂ on C; hydrogen / tetrahydrofuran / 3 h / 20 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

6.2: 0.5 h / -78 - 0 °C / Inert atmosphere

7.1: diethyl ether / 18 h / -78 - -20 °C / Inert atmosphere

7.2: 1 h / 0 °C / pH 7 / aq. buffer

8.1: hydrogenchloride; water / tetrahydrofuran / 4 h / 20 °C

With 1H-imidazole; hydrogenchloride; samarium diiodide; oxalyl dichloride; 10% Pd(OH)₂ on C; water; hydrogen; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 2.1: Aldol reaction / 3.1: Evans-Tishchenko reduction / 6.1: Swern oxidation / 6.2: Swern oxidation / 7.1: Aldol reaction;
DOI:10.1016/j.tet.2011.09.012