(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol

Base Information

• Chemical Name: (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol
• CAS No.: 941715-39-5
• Molecular Formula: C₂₇H₄₁NO₂Si
• Molecular Weight: 439.714
• Mol file: 941715-39-5.mol

Synonyms:(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol

Chemical Property of (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol

There total 1 articles about (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol 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: 73.0%

4-but-1-enylmagnesium bromide (7103-09-5) + (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde (125654-82-2) → (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol (941715-39-5) + (2R,3S)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol

Guidance literature:

In diethyl ether; at 0 ℃;

DOI:10.1002/ejoc.200601009

Reference yield: 87.0%

(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol (941715-39-5) + acetic anhydride (108-24-7) → (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-yl acetate (941715-45-3)

Guidance literature:

With dmap; In dichloromethane; for 1.5h;

DOI:10.1002/ejoc.200601009

Reference yield:

(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-ol (941715-39-5) → (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-oxooctadec-3-yl acetate (941715-55-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / DMAP / CH₂Cl₂ / 1.5 h

2: NMO / OsO₄ / acetone; H₂O; toluene / 8 h / 20 °C

3: 1.26 g / NaIO₄/SiO₂ / CH₂Cl₂ / 1 h / 0 °C

4: diethyl ether / -78 °C

5: 993 mg / SO₃*Py; triethylamine / dimethylsulfoxide; CH₂Cl₂ / 20 °C

With dmap; sodium periodate; N-methyl-2-indolinone; pyridine-SO₃ complex; silica gel; triethylamine; osmium(VIII) oxide; In diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone; toluene;

DOI:10.1002/ejoc.200601009

upstream raw materials:

4-but-1-enylmagnesium bromide

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde

Downstream raw materials:

(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-hepten-3-yl acetate

(2S,3R)-3-acetoxy-2-(dibenzylamino)-6-oxooctadecyl acetate

(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-oxohex-3-yl acetate

(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(dibenzylamino)-6-oxooctadec-3-yl acetate