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

Base Information

• Chemical Name: (2R),(5RS)-1-O-Benzyl-2-O-tert-butyldimethylsilyl-1,2,5-decantriol
• CAS No.: 381719-00-2
• Molecular Formula: C₂₃H₄₂O₃Si
• Molecular Weight: 394.67
• Mol file: 381719-00-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (2R),(5RS)-1-O-Benzyl-2-O-tert-butyldimethylsilyl-1,2,5-decantriol 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: 90.0%

n-pentylmagnesium bromide (693-25-4) + (R)-5-O-Benzyl-4-O-tert-butyldimethylsilyl-4,5-dihydroxypentanal (381718-99-6) → (2R),(5RS)-1-O-Benzyl-2-O-tert-butyldimethylsilyl-1,2,5-decantriol (381719-00-2)

Guidance literature:

In diethyl ether; at 20 ℃; for 4h;

DOI:10.1055/s-2001-16789

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (2R),(5RS)-1-O-Benzyl-2-O-tert-butyldimethylsilyl-1,2,5-decantriol (381719-00-2)

Guidance literature:

Multi-step reaction with 7 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

7: 90 percent / diethyl ether / 4 h / 20 °C

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

DOI:10.1055/s-2001-16789

Reference yield:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) → (2R),(5RS)-1-O-Benzyl-2-O-tert-butyldimethylsilyl-1,2,5-decantriol (381719-00-2)

Guidance literature:

Multi-step reaction with 7 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

7: 90 percent / diethyl ether / 4 h / 20 °C

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

DOI:10.1055/s-2001-16789

upstream raw materials:

n-pentylmagnesium bromide

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

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

O-benzyl 2,2,2-trichloroacetimidate

Downstream raw materials:

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

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

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