(2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde

Base Information

• Chemical Name: (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde
• CAS No.: 163041-09-6
• Molecular Formula: C₂₄H₃₄O₄Si
• Molecular Weight: 414.617
• Mol file: 163041-09-6.mol

Synonyms:(2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde

Chemical Property of (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde

There total 9 articles about (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde 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: 72.0%

(2'S,3'R,4S)-4-benzyl-3-[2',4'-bis(benzyloxy)-3'-(tert-butyldimethylsilanyloxy)-1'-hydroxybutyl]-5,5-dimethyloxazolidin-2-one (846542-04-9) → (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde (163041-09-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.25h;

DOI:10.1039/b415943h

Reference yield: 71.0%

(S)-4-Benzyl-3-[(2S,3R)-2,4-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-butyl]-5,5-dimethyl-oxazolidin-2-one (496877-73-7) → (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde (163041-09-6)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.25h;

DOI:10.1055/s-2002-34215

Reference yield:

benzyloxyacetoaldehyde (60656-87-3) → (2S,3R)-2,4-bis(benzyloxy)-3-(tert-butyldimethylsilanyloxy)butyraldehyde (163041-09-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / Et₂BOTf; i-Pr₂NEt / CH₂Cl₂; hexane / -78 - 0 °C

2: 90 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C

3: 94 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

4: 72 percent / aq. K₂CO₃ / methanol / 0.25 h / 20 °C

With 1H-imidazole; dmap; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b415943h

upstream raw materials:

1,3-O-Dibenzyl-2-O-(tert-butyldimethylsilyl)threitol

(S)-4-Benzyl-3-[(2S,3R)-2,4-bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-butyl]-5,5-dimethyl-oxazolidin-2-one

(2'S,3'R,4S)-4-benzyl-3-[2',4'-bis(benzyloxy)-3'-(tert-butyldimethylsilanyloxy)-1'-hydroxybutyl]-5,5-dimethyloxazolidin-2-one

benzyloxyacetoaldehyde

Downstream raw materials:

(2R,3R,4R,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-4-ol

(2R,3R,4S,6S)-3-Benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-tetrahydro-pyran-4-ol

(2R,4R,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol

(2R,4S,5R,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-tetrahydro-pyran-3-ylmethyl)-2-methylsulfanyl-tetrahydro-pyran-4-ol