(1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate

Base Information

• Chemical Name: (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate
• CAS No.: 1448328-63-9
• Molecular Formula: C₅₆H₉₃NO₁₂Si₃
• Molecular Weight: 1056.61
• Mol file: 1448328-63-9.mol

Synonyms:(1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate

Chemical Property of (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate

There total 18 articles about (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate 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: 99.0%

triethylsilyl chloride (994-30-9) + (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-4-hydroxy-5-methyl-6-oxohexyl acetate (1448328-62-8) → (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate (1448328-63-9)

Guidance literature:

With 1H-imidazole; dmap; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1002/anie.201208919

Reference yield:

(2R,3S,7S,E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)tetradec-10-en-5-yn-7-ol (1448328-52-6) → (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate (1448328-63-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: iron(III)-acetylacetonate; 1,2-bis-(diphenylphosphino)ethane / tetrahydrofuran / 0.17 h / -78 °C

1.2: 20 h / -78 - 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: zinc trifluoromethanesulfonate; pyridine N-oxide; citric acid; potassium osmate(VI) dihydrate / acetonitrile; aq. phosphate buffer / 36 h / 60 - 80 °C

4.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C

5.1: pyridine; dmap / dichloromethane / 18 h / 0 - 20 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -78 - 20 °C

7.1: hydrogen / ethyl acetate / 8 h / 30 °C

8.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -50 - -10 °C

9.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.25 h / -78 - 0 °C

9.2: 3 h / 0 °C

10.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; pyridine N-oxide; 2,6-dimethylpyridine; dmap; potassium osmate(VI) dihydrate; iron(III)-acetylacetonate; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; citric acid; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; ethyl acetate; acetonitrile; 9.1: |Evans Aldol Reaction / 9.2: |Evans Aldol Reaction;

DOI:10.1002/anie.201208919

Reference yield:

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-dien-7-ol (1448328-54-8) → (1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate (1448328-63-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

2.1: zinc trifluoromethanesulfonate; pyridine N-oxide; citric acid; potassium osmate(VI) dihydrate / acetonitrile; aq. phosphate buffer / 36 h / 60 - 80 °C

3.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C

4.1: pyridine; dmap / dichloromethane / 18 h / 0 - 20 °C

5.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -78 - 20 °C

6.1: hydrogen / ethyl acetate / 8 h / 30 °C

7.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / -50 - -10 °C

8.1: triethylamine; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.25 h / -78 - 0 °C

8.2: 3 h / 0 °C

9.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; pyridine N-oxide; 2,6-dimethylpyridine; dmap; potassium osmate(VI) dihydrate; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; sulfur trioxide pyridine complex; zinc trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; In tetrahydrofuran; aq. phosphate buffer; dichloromethane; ethyl acetate; acetonitrile; 8.1: |Evans Aldol Reaction / 8.2: |Evans Aldol Reaction;

DOI:10.1002/anie.201208919

upstream raw materials:

(2R,3S,7S,E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)tetradec-10-en-5-yn-7-ol

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-dien-7-ol

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

(R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol

Downstream raw materials:

(R)-4-benzyl-3-((2R,3S,6R)-6-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-6-hydroxy-2-methyl-3-((triethylsilyl)oxy)hexanoyl)oxazolidin-2-one

(1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl chloromethanesulfonate

(R)-4-benzyl-3-((R)-2-((2S,5S,7S)-2-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-hydroxy-2-methyltetrahydrofuran-2-yl)methyl)-1,6-dioxaspiro[4.5]decan-7-yl)propanoyl)oxazolidin-2-one

(R)-4-benzyl-3-((R)-2-((2S,5S,7S)-2-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)-1,6-dioxaspiro[4.5]decan-7-yl)propanoyl)oxazolidin-2-one