1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

Base Information

Chemical Name:1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione
CAS No.:126789-29-5
Molecular Formula:C₃₄H₅₅NO₉Si
Molecular Weight:649.898
Hs Code.:

1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

Synonyms:1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

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Chemical Property of 1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

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Technology Process of 1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

There total 7 articles about 1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione 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: 75.0%

: 126789-28-4
(4R,6S,7R,8S,10R)-1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-6,8-dimethoxy-4,10-dimethyl-7-triethylsilanyloxy-11-triisopropylsilanyloxy-undecane-1,2,3-trione

: 126789-29-5
1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

Guidance literature:: With water; trifluoroacetic acid; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ja00164a023

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 126789-29-5
1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 1.) AgNO₃, NCS, 2,6-lutidine, 2.) glyoxylic acid hydrate, HOAc / 1.) CH₃OH, THF, 20 deg C, 2.) CH₂Cl₂, 40 deg C

3: 1.) Et₃N, n-Bu₂BOTf / 1.) 0 deg C

4: 64 percent / Zn, HOAc / tetrahydrofuran / 20 °C

5: 84 percent / (COCl)2, Et₃N / CH₂Cl₂ / -78 °C

6: 75 percent / TFA, H₂O / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; N-chloro-succinimide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; water; silver nitrate; acetic acid; triethylamine; Glyoxilic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00164a023

Reference yield:

: 126789-11-5
(2R,4S,5R,6S,8R)-8-[1,3]Dithian-2-yl-4,6-dimethoxy-2-methyl-5-triethylsilanyloxy-nonan-1-ol

: 126789-29-5
1-((S)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-[(2R,3R,5S,6R)-2-hydroxy-5-methoxy-6-((1R,3R)-1-methoxy-3-methyl-4-triisopropylsilanyloxy-butyl)-3-methyl-tetrahydro-pyran-2-yl]-ethane-1,2-dione

Guidance literature:: Multi-step reaction with 6 steps

1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2: 1.) AgNO₃, NCS, 2,6-lutidine, 2.) glyoxylic acid hydrate, HOAc / 1.) CH₃OH, THF, 20 deg C, 2.) CH₂Cl₂, 40 deg C

3: 1.) Et₃N, n-Bu₂BOTf / 1.) 0 deg C

4: 64 percent / Zn, HOAc / tetrahydrofuran / 20 °C

5: 84 percent / (COCl)2, Et₃N / CH₂Cl₂ / -78 °C

6: 75 percent / TFA, H₂O / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; N-chloro-succinimide; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; water; silver nitrate; acetic acid; triethylamine; Glyoxilic acid; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja00164a023