(4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

Base Information

Chemical Name:(4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one
CAS No.:871236-56-5
Molecular Formula:C₃₄H₅₁NO₆Si
Molecular Weight:597.868
Hs Code.:

Synonyms:(4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

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Chemical Property of (4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

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Technology Process of (4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

There total 10 articles about (4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-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: 74.0%

: 74-88-4
methyl iodide

: 871236-56-5
(4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

Guidance literature:: (4R)-3-((4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoyl)-4-benzyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

methyl iodide; In tetrahydrofuran; at -78 - 25 ℃; for 15h;

Reference yield: 74.0%

: 871236-55-4
(4R)-3-((4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoyl)-4-benzyloxazolidin-2-one

: 74-88-4
methyl iodide

: 871236-56-5
(4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

Guidance literature:: (4R)-3-((4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylheptanoyl)-4-benzyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.75h;

methyl iodide; In tetrahydrofuran; at -78 - 25 ℃; Further stages.;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 792911-22-9
(-)-(2S,3R,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentan-1-ol

: 871236-56-5
(4R)-3-((2R,4S,5R,6S)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptanoyl)-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 20 °C

2.1: NaH / tetrahydrofuran / cooling

2.2: 8.96 g / tetrahydrofuran / cooling

3.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

4.1: aq. LiOH / tetrahydrofuran / 6 h / 60 °C

5.1: Et₃N / tetrahydrofuran / -78 - 0 °C

5.2: 7.91 g / LiCl / tetrahydrofuran / 0 - 20 °C

6.1: NaHMDS / tetrahydrofuran / 0.75 h / -78 °C

6.2: 74 percent / tetrahydrofuran / -78 - 25 °C

With lithium hydroxide; sodium tetrahydroborate; sodium hexamethyldisilazane; sodium hydride; dimethyl sulfoxide; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033