Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide

Base Information

• Chemical Name: Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide
• CAS No.: 383418-15-3
• Molecular Formula: C₂₈H₅₁NO₃Si
• Molecular Weight: 477.803
• Mol file: 383418-15-3.mol

Synonyms:Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide

Chemical Property of Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide

There total 8 articles about Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide 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:

dodecanoic acid [1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-3-phenyl-propyl]-amide (383418-13-1) → Dodecanoic acid [(1R,3S)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide + Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide (383418-15-3)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4039(01)01658-6

Reference yield:

4-(tert-butyl-dimethyl-silanyloxy)-3-dodecanoylamino-thiobutyric acid S-ethyl ester (383418-11-9) → Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide (383418-15-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 37 percent / tetrahydrofuran / 1 h / -15 °C

2: L-Selectride / tetrahydrofuran / 1 h / -78 °C

With L-Selectride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)01658-6

Reference yield:

tert-butyldimethylsiloxyacetaldehyde (102191-92-4) → Dodecanoic acid [(1R,3R)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-3-phenyl-propyl]-amide (383418-15-3)

Guidance literature:

Multi-step reaction with 5 steps

1: Zr(Ot-Bu)4; (R)-6,6'-Br₂BINOL; N-methylimidazole / MS₄A / CH₂Cl₂ / -45 °C

2: 61 percent / CAN / acetonitrile; H₂O / 0.5 h / 0 °C

3: 81 percent / Et₃N / CH₂Cl₂ / 20 °C

4: 37 percent / tetrahydrofuran / 1 h / -15 °C

5: L-Selectride / tetrahydrofuran / 1 h / -78 °C

With 1-methyl-1H-imidazole; ammonium cerium(IV) nitrate; (R)-6,6'-dibromo-1,1'-binaphth-2-ol; L-Selectride; zirconium(IV) tert-butoxide; triethylamine; MS₄A; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1: Mannich-type reaction;

DOI:10.1016/S0040-4039(01)01658-6

upstream raw materials:

dodecanoic acid [1-(tert-butyl-dimethyl-silanyloxymethyl)-3-oxo-3-phenyl-propyl]-amide

tert-butyldimethylsiloxyacetaldehyde

3-amino-4-(tert-butyl-dimethyl-silanyloxy)-thiobutyric acid S-ethyl ester

4-(tert-butyl-dimethyl-silanyloxy)-3-(2-hydroxy-6-methyl-phenylamino)-thiobutyric acid S-ethyl ester

Downstream raw materials:

(1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylprop-1-yl)dodecanamide