(2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol

Base Information

• Chemical Name: (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol
• CAS No.: 1647153-46-5
• Molecular Formula: C₃₁H₄₇NO₄Si
• Molecular Weight: 525.804
• Mol file: 1647153-46-5.mol

Synonyms:(2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol

Chemical Property of (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol

There total 3 articles about (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol 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: 82.0%

levulinic acid (123-76-2) + (2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentan-3-ol (188802-09-7) → (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol (1647153-46-5)

Guidance literature:

levulinic acid; With dmap; diisopropyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.25h;

(2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentan-3-ol; In dichloromethane; at 0 - 20 ℃; for 14h;

DOI:10.3762/bjoc.10.113

Reference yield:

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde (188840-00-8) → (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol (1647153-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrahydrofuran; diethyl ether

2.1: dmap; diisopropyl-carbodiimide / dichloromethane / 0.25 h / 0 °C

2.2: 14 h / 0 - 20 °C

With dmap; diisopropyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: |Grignard Reaction;

DOI:10.3762/bjoc.10.113

Reference yield:

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propan-1-ol (188802-16-6) → (2R,3S)-2-(dibenzylamino)-1-O-(tert-butyldimethylsilyl)-3-O-levulinyl-4-methylpentane-1,3-diol (1647153-46-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane

2.1: tetrahydrofuran; diethyl ether

3.1: dmap; diisopropyl-carbodiimide / dichloromethane / 0.25 h / 0 °C

3.2: 14 h / 0 - 20 °C

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; diisopropyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: |Swern Oxidation / 2.1: |Grignard Reaction;

DOI:10.3762/bjoc.10.113

upstream raw materials:

levulinic acid

(2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentan-3-ol

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propan-1-ol

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