(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

Base Information

• Chemical Name: (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
• CAS No.: 1289513-26-3
• Molecular Formula: C₃₈H₅₆O₈Si
• Molecular Weight: 668.943
• Mol file: 1289513-26-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 10 articles about (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 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: 97.0%

(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 (1289513-22-9) + vinyl magnesium bromide (1826-67-1) → (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 (1289513-26-3)

Guidance literature:

(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; vinyl magnesium bromide; In tetrahydrofuran; at -78 ℃; for 0.333333h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; at -78 - 20 ℃; optical yield given as %de; 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) → (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 (1289513-26-3)

Guidance literature:

Multi-step reaction with 9 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

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.08 h / -50 °C / Inert atmosphere

8.2: 0.33 h / -40 °C / Inert atmosphere

8.3: -40 - 20 °C / Inert atmosphere

9.1: tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

9.2: -78 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; oxalyl dichloride; trityl tetrafluoroborate; diisobutylaluminium hydride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 8.1: Swern oxidation / 8.2: Swern oxidation / 8.3: Swern oxidation;

DOI:10.1002/ejoc.201001411

Reference yield:

(2S,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-5-{(S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-methoxybenzyl)oxy]ethyl}-5-methyltetrahydrofuran-2-carbaldehyde (1289513-06-9) → (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 (1289513-26-3)

Guidance literature:

Multi-step reaction with 6 steps

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

1.2: 0.17 h / -78 °C / Inert atmosphere

1.3: -78 - 20 °C / Inert atmosphere

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

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

3.2: 0.05 h / -78 °C / Inert atmosphere

3.3: -78 - 20 °C / Inert atmosphere

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

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.08 h / -50 °C / Inert atmosphere

5.2: 0.33 h / -40 °C / Inert atmosphere

5.3: -40 - 20 °C / Inert atmosphere

6.1: tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

With oxalyl dichloride; pyridine hydrogenfluoride; ozone; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; 5.1: Swern oxidation / 5.2: Swern oxidation / 5.3: Swern oxidation;

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