(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

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 chloromethanesulfonate
• CAS No.: 1448328-65-1
• Molecular Formula: C₅₅H₉₂ClNO₁₃SSi₃
• Molecular Weight: 1127.11
• Mol file: 1448328-65-1.mol

Synonyms:

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 chloromethanesulfonate

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 chloromethanesulfonate

There total 19 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 chloromethanesulfonate 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:

(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 chloromethanesulfonate (1448328-65-1)

Guidance literature:

Multi-step reaction with 12 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

11.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 3.5 h / -78 °C

12.1: pyridine / 2.5 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; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; citric acid; In tetrahydrofuran; aq. phosphate buffer; hexane; 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 chloromethanesulfonate (1448328-65-1)

Guidance literature:

Multi-step reaction with 11 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

10.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 3.5 h / -78 °C

11.1: pyridine / 2.5 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; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; citric acid; In tetrahydrofuran; aq. phosphate buffer; hexane; dichloromethane; ethyl acetate; acetonitrile; 8.1: |Evans Aldol Reaction / 8.2: |Evans Aldol Reaction;

DOI:10.1002/anie.201208919

Reference yield:

(R)-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-hydroxybutyl acetate (1448328-60-6) → (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 chloromethanesulfonate (1448328-65-1)

Guidance literature:

Multi-step reaction with 5 steps

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

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

2.2: 3 h / 0 °C

3.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 3.5 h / -78 °C

5.1: pyridine / 2.5 h / 0 - 20 °C

With pyridine; 1H-imidazole; dmap; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: |Evans Aldol Reaction / 2.2: |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-((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

C₅₄H₉₁NO₁₁Si₃

Refernces