(R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

Base Information

Chemical Name:(R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one
CAS No.:902480-50-6
Molecular Formula:C₃₀H₄₉NO₆Si
Molecular Weight:547.808
Hs Code.:

Synonyms:(R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

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Chemical Property of (R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

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Technology Process of (R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

There total 4 articles about (R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one 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:

: 902480-49-3
(2S,3S,4R)-5-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-methoxy-2-methyl-5-oxo-3-triisopropylsilanyloxy-pentanal

: 624-64-6
trans-2-Butene

: 902480-60-8
(3R,4S,5R,6S)-3-Methoxy-5-methyl-6-((S)-1-methyl-allyl)-4-triisopropylsilanyloxy-tetrahydro-pyran-2-one

: 902480-50-6
(R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

Guidance literature:: trans-2-Butene; With n-butyllithium; 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; potassium tert-butylate; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 - -40 ℃;

(2S,3S,4R)-5-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-4-methoxy-2-methyl-5-oxo-3-triisopropylsilanyloxy-pentanal; In tetrahydrofuran; at -78 ℃; for 5h;
DOI:10.1021/ol060882s

Reference yield:

: 902480-48-2
(R)-4-Benzyl-3-[(2R,3S,4R)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-4-methyl-3-triisopropylsilanyloxy-pentanoyl]-oxazolidin-2-one

: 902480-50-6
(R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: 82 percent / PCC; MgSO₄; Celite / CH₂Cl₂ / 72 h / 20 °C

2.1: t-BuOK; n-BuLi; 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane / BF₃*OEt₂ / tetrahydrofuran / -78 - -40 °C

2.2: tetrahydrofuran / 5 h / -78 °C

With n-butyllithium; 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Celite; potassium tert-butylate; magnesium sulfate; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol060882s

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 902480-50-6
(R)-4-Benzyl-3-((2R,3S,4R,5S,6S)-5-hydroxy-2-methoxy-4,6-dimethyl-3-triisopropylsilanyloxy-oct-7-enoyl)-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: dibutylboron triflate; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

1.2: CH₂Cl₂ / 4 h / 0 °C

1.3: 53 percent / triethylamine / CH₂Cl₂ / 3 h / 0 °C

2.1: 82 percent / PCC; MgSO₄; Celite / CH₂Cl₂ / 72 h / 20 °C

3.1: t-BuOK; n-BuLi; 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane / BF₃*OEt₂ / tetrahydrofuran / -78 - -40 °C

3.2: tetrahydrofuran / 5 h / -78 °C

With n-butyllithium; 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; Celite; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; magnesium sulfate; triethylamine; pyridinium chlorochromate; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; 1.2: Evans aldol condensation;
DOI:10.1021/ol060882s