(2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal

Base Information

• Chemical Name: (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal
• CAS No.: 1310802-67-5
• Molecular Formula: C₂₆H₃₈O₄Si
• Molecular Weight: 442.671
• Mol file: 1310802-67-5.mol

Synonyms:(2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal

Chemical Property of (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal

There total 8 articles about (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal 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: 83.0%

(2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutan-1-ol (1310802-60-8) → (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal (1310802-67-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1016/j.tetlet.2011.03.154

Reference yield:

(2R,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-methylpropan-1-ol (954114-83-1) → (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal (1310802-67-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: Dess-Martin periodane / dichloromethane / 26 h / 20 °C

2.1: tetrahydrofuran / 3 h / 0 °C

3.1: Dess-Martin periodane / dichloromethane / 15 h / 20 °C

4.1: tetrahydrofuran; toluene / 5 h / -40 °C

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 0 - 20 °C

5.2: 2 h

6.1: Dess-Martin periodane / dichloromethane / 15 h / 20 °C

With Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; toluene; 1.1: Dess-Martin oxidation / 2.1: Grignard reaction / 3.1: Dess-Martin oxidation / 6.1: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2011.03.154

Reference yield:

C25H38O4Si (1310802-64-2) → (2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutanal (1310802-67-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodane / dichloromethane / 15 h / 20 °C

2.1: tetrahydrofuran; toluene / 5 h / -40 °C

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 5 h / 0 - 20 °C

3.2: 2 h

4.1: Dess-Martin periodane / dichloromethane / 15 h / 20 °C

With Dess-Martin periodane; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane; toluene; 1.1: Dess-Martin oxidation / 4.1: Dess-Martin oxidation;

DOI:10.1016/j.tetlet.2011.03.154

upstream raw materials:

(2R,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-methylpropan-1-ol

(2S,3R,4S)-4-(4-(benzyloxy)-3-methoxyphenyl)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethylbutan-1-ol

C₃₄H₄₃NO₆Si

(2S,3S)-3-(4-(benzyloxy)-3-methoxyphenyl)-3-((tert-butyldimethylsilyl)oxy)-2-methylpropanal

Downstream raw materials:

C₂₇H₃₀O₆

C₂₆H₃₈O₆Si

C₃₃H₄₂O₇Si

C₂₇H₂₈O₇

Refernces

• 1、 Harada, Kenichi,Horiuchi, Hiroki,Tanabe, Kazuma,Carter, Rich G.,Esumi, Tomoyuki,Kubo, Miwa,Hioki, Hideaki,Fukuyama, Yoshiyasu. "Asymmetric synthesis of (-)-chicanine using a highly regioselective intramolecular Mitsunobu reaction and revision of its absolute configuration". . p. 3005 - 3008. Retrieved 2011/06/23.