(2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal

Base Information

• Chemical Name: (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal
• CAS No.: 1407163-67-0
• Molecular Formula: C₁₇H₂₈O₃Si
• Molecular Weight: 308.493
• Mol file: 1407163-67-0.mol

Synonyms:(2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal

Chemical Property of (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal

There total 7 articles about (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal 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: 92.0%

(2R,3S)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)butan-1-ol (1407163-79-4) → (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal (1407163-67-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1039/c2ob26396c

Reference yield: 82.0%

{[(2S,3R)-3-(benzyloxy)pent-4-en-2-yl]oxy}(tert-butyl)dimethylsilane (1437598-70-3) → (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal (1407163-67-0)

Guidance literature:

With dimethylsulfide; ozone; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/ejoc.201201246

Reference yield:

(1S)-1-((4R)-2-phenyl-1,3-dioxolan-4-yl)ethyl benzoate (1407163-76-1) → (2S,3S)-2-(benzyloxy)-3-[(tert-butyldimethylsilyl)oxy]butanal (1407163-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium carbonate / methanol / 0.5 h / 20 °C

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

3: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -40 °C

4: Dess-Martin periodane / dichloromethane / 0.5 h / 0 - 20 °C

With 1H-imidazole; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; In methanol; dichloromethane; toluene;

DOI:10.1039/c2ob26396c

upstream raw materials:

(1S)-1-((4R)-2-phenyl-1,3-dioxolan-4-yl)ethyl benzoate

(1S)-1-((4R)-2-phenyl-1,3-dioxolan-4-yl)ethanol

tert-butyldimethyl((1S)-1-((4R)-2-phenyl-1,3-dioxolan-4-yl)ethoxy)silane

(2R,3S)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)butan-1-ol

Downstream raw materials:

(5S,6S,10S,13R)-6,10-bis(benzyloxy)-2,2,3,3,5,13,15,15,16,16-decamethyl-4,14-dioxa-3,15-disilaheptadec-8-yn-7-one

(2S,3S,6R,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

(2S,3S,6S,8R,11S)-3,11-bis(benzyloxy)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-one

(2S,3S,7S,10R)-3,7-bis(benzyloxy)-2,10-dihydroxyundec-5-yn-4-one