(R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal

Base Information

• Chemical Name: (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal
• CAS No.: 381718-99-6
• Molecular Formula: C₁₈H₃₀O₃Si
• Molecular Weight: 322.52
• Mol file: 381718-99-6.mol

Synonyms:(R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal

Chemical Property of (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal

There total 8 articles about (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal 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: 96.0%

C18H28O3Si → (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal (381718-99-6)

Guidance literature:

With 20 % Pd(OH)2/C; hydrogen; In benzene; at 20 ℃; for 0.75h;

DOI:10.1055/s-0031-1291004

Reference yield:

5-benzyloxy 4R-t-butyldimethylsiloxy 1-pentanol (98892-19-4) → (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal (381718-99-6)

Guidance literature:

With sodium acetate; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1055/s-2001-16789

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal (381718-99-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / CF₃SO₃H / CH₂Cl₂; hexane / 0.5 h / 0 °C

2: aq. NaOH / 1 h / 20 °C

3: TBABr / acetone / 8 h / 20 °C

4: imidazole / tetrahydrofuran / 15 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 4 h / 20 °C

6: PCC; AcONa / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; trifluorormethanesulfonic acid; tetrabutylammomium bromide; sodium acetate; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1055/s-2001-16789

upstream raw materials:

5-benzyloxy 4R-t-butyldimethylsiloxy 1-pentanol

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

O-benzyl 2,2,2-trichloroacetimidate

(R)-(-)-γ-benzyloxymethyl-γ-butyrolactone

Downstream raw materials:

(2R),(5RS)-1-O-Benzyl-2-O-tert-butyldimethylsilyl-1,2,5-decantriol

(R)-1-O-Benzyl-5-ethylenedithio-1,2-decandiol

1-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-decan-5-one

(R)-1-O-Benzyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-ethylenedithio-1,2-decandiol