(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

Base Information

Chemical Name:(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one
CAS No.:565229-03-0
Molecular Formula:C₃₆H₅₅NO₈Si
Molecular Weight:657.92
Hs Code.:

Synonyms:(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

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Chemical Property of (4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

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Technology Process of (4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

There total 9 articles about (4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]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: 92.0%

: 565229-77-8
(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-8-(4-methoxybenzyloxy)-2,4-dimethyloctanoyl]oxazolidin-2-one

: 565229-03-0
(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

Guidance literature:: With chloromethyl methyl ether; N-ethyl-N,N-diisopropylamine; In dichloromethane; Heating / reflux;

Reference yield: 92.0%

: 107-30-2
chloromethyl methyl ether

: 565229-77-8
(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-3-hydroxy-8-(4-methoxybenzyloxy)-2,4-dimethyloctanoyl]oxazolidin-2-one

: 565229-03-0
(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; Heating;
DOI:10.1021/jm0204136

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 565229-03-0
(4R)-4-benzyl-3-[(2R,3S,4R,5S)-5-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-3-methoxymethoxy-2,4-dimethyloctanoyl]oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: 92 percent / NaH / dimethylformamide

2.1: pyridinium sulfur trioxide; N,N-diisopropylethylamine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

3.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

3.3: 87 percent / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / 0 °C / pH 7.0

4.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

5.1: 78 percent / lithium borohydride / tetrahydrofuran; methanol / 3.33 h / 0 - 20 °C

6.1: pyridinium sulfur trioxide; N,N-diisopropylethylamine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

7.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

7.3: 2.29 g / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / pH 7.0

8.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / Heating

With 2,6-dimethylpyridine; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jm0204136