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

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-4-acetoxy-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2-ol
CAS No.:1352832-13-3
Molecular Formula:C₂₉H₃₆O₉
Molecular Weight:528.599
Hs Code.:

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

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

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

There total 13 articles about (2R,3R,4R,5S,6S)-4-acetoxy-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2-ol 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: 84.0%

: 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

: 108-24-7
acetic anhydride

: 1352832-13-3
(2R,3R,4R,5S,6S)-4-acetoxy-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2-ol

Guidance literature:: With pyridine; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.012

Reference yield:

: 273944-68-6
C₂₄H₃₅BO₄

: 1352832-13-3
(2R,3R,4R,5S,6S)-4-acetoxy-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: pyridine / 3 h / 20 °C / Inert atmosphere

With pyridine; 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

: 1352832-13-3
(2R,3R,4R,5S,6S)-4-acetoxy-2-((1'S)-1'-benzoyloxyethyl)-6-[(1''R,2''R)-2''-benzoyloxy-1''-methylprop-1''-yl]-3-methoxy-5-methyltetrahydropyran-2-ol

Guidance literature:: Multi-step reaction with 9 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

9.1: pyridine / 3 h / 20 °C / Inert atmosphere

With pyridine; 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