(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

Base Information

• Chemical Name: (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
• CAS No.: 1448328-66-2
• Molecular Formula: C₄₀H₆₇NO₉Si₂
• Molecular Weight: 762.144
• Mol file: 1448328-66-2.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 20 articles about (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 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) → (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 (1448328-66-2)

Guidance literature:

Multi-step reaction with 13 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

13.1: zinc diacetate; 1,1,1,3',3',3'-hexafluoro-propanol / 6 h / 30 °C / Sealed tube

With pyridine; 1H-imidazole; pyridine N-oxide; 2,6-dimethylpyridine; dmap; potassium osmate(VI) dihydrate; iron(III)-acetylacetonate; 1,1,1,3',3',3'-hexafluoro-propanol; di-n-butylboryl trifluoromethanesulfonate; zinc diacetate; 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) → (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 (1448328-66-2)

Guidance literature:

Multi-step reaction with 12 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

12.1: zinc diacetate; 1,1,1,3',3',3'-hexafluoro-propanol / 6 h / 30 °C / Sealed tube

With pyridine; 1H-imidazole; pyridine N-oxide; 2,6-dimethylpyridine; dmap; potassium osmate(VI) dihydrate; 1,1,1,3',3',3'-hexafluoro-propanol; di-n-butylboryl trifluoromethanesulfonate; zinc diacetate; 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)-4-(benzyloxy)-1-((2R,5S)-5-((S)-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)(hydroxy)methyl)tetrahydrofuran-2-yl)butan-1-ol (1448328-57-1) → (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 (1448328-66-2)

Guidance literature:

Multi-step reaction with 9 steps

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

2.1: 2,6-dimethylpyridine / dichloromethane / 12 h / -78 - 20 °C

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

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

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

5.2: 3 h / 0 °C

6.1: 1H-imidazole; dmap / dichloromethane / 2 h / 0 - 20 °C

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

8.1: pyridine / 2.5 h / 0 - 20 °C

9.1: zinc diacetate; 1,1,1,3',3',3'-hexafluoro-propanol / 6 h / 30 °C / Sealed tube

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; 1,1,1,3',3',3'-hexafluoro-propanol; di-n-butylboryl trifluoromethanesulfonate; zinc diacetate; hydrogen; sulfur trioxide pyridine complex; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 5.1: |Evans Aldol Reaction / 5.2: |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