(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol

Base Information

• Chemical Name: (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol
• CAS No.: 1289513-19-4
• Molecular Formula: C₃₆H₅₄O₈Si
• Molecular Weight: 642.905
• Mol file: 1289513-19-4.mol

Synonyms:(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol

Chemical Property of (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol

There total 8 articles about (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol 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: 89.0%

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy](tert-butyl)dimethylsilane (1289513-17-2) → (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol (1289513-19-4)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.201001411

Reference yield:

(2S,3R,5R)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-hydroxy-5-methyl-tetrahydro-furan-2-carboxylic acid methyl ester (1063693-99-1) → (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol (1289513-19-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.92 h / -78 °C / Inert atmosphere

2.1: trityl tetrafluoroborate / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -90 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

4.2: 0.17 h / -78 °C / Inert atmosphere

4.3: -78 - 20 °C / Inert atmosphere

5.1: diethyl ether / 0.33 h / -78 - 0 °C / Inert atmosphere

6.1: ozone / dichloromethane / 0.01 h / -78 °C / Inert atmosphere

6.2: 0.05 h / -78 °C / Inert atmosphere

6.3: -78 - 20 °C / Inert atmosphere

7.1: pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; trityl tetrafluoroborate; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1002/ejoc.201001411

Reference yield:

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-hydroxyethyl}-5-methyltetrahydrofuran-2-carboxylate (1289513-04-7) → (S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]ethanol (1289513-19-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: trityl tetrafluoroborate / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.33 h / -90 °C / Inert atmosphere

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

3.2: 0.17 h / -78 °C / Inert atmosphere

3.3: -78 - 20 °C / Inert atmosphere

4.1: diethyl ether / 0.33 h / -78 - 0 °C / Inert atmosphere

5.1: ozone / dichloromethane / 0.01 h / -78 °C / Inert atmosphere

5.2: 0.05 h / -78 °C / Inert atmosphere

5.3: -78 - 20 °C / Inert atmosphere

6.1: pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

With trityl tetrafluoroborate; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1002/ejoc.201001411

upstream raw materials:

(2S,3R,5R)-5-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-3-hydroxy-5-methyl-tetrahydro-furan-2-carboxylic acid methyl ester

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-hydroxyethyl}-5-methyltetrahydrofuran-2-carboxylate

(2S,3R,5R)-methyl 3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carboxylate

(2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde

Downstream raw materials:

(R)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(4-methoxybenzyl)oxy]acetaldehyde

(1S,2R)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(4-methoxybenzyl)oxy]but-3-en-2-ol