(2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol

Base Information

• Chemical Name: (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol
• CAS No.: 432038-19-2
• Molecular Formula: C₃₁H₅₄O₃Si
• Molecular Weight: 502.853
• Mol file: 432038-19-2.mol

Synonyms:(2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol

Chemical Property of (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol

There total 3 articles about (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-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: 90.0%

(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(Z)-2-(tert-butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxane (432038-18-1) → (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol (432038-19-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1039/b111071n

Reference yield:

Phenyl 2,3,4-tris-O-(tert-butyldimethylsilyl)-1-thio-β-D-xylopyranoside (331456-61-2) → (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol (432038-19-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 89 percent / MeLi / tetrahydrofuran / 0.33 h / -78 °C

3: 82 percent / p-TsOH / CH₂Cl₂ / 2 h / 20 °C

4: 90 percent / Bu₄NF / tetrahydrofuran / 12 h / 20 °C

With tetrabutyl ammonium fluoride; methyllithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1039/b111071n

Reference yield:

(2S,3R,4S,5R)-2-Benzenesulfinyl-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran → (2S,4R,5R)-4-[(Z)-2-(tert-Butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxan-5-ol (432038-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 97 percent / LDA / tetrahydrofuran / 2 h / -78 °C

2.1: t-BuLi / tetrahydrofuran; diethyl ether / 0.08 h / -78 °C

2.2: CuBr*SMe₂ / diethyl ether; various solvent(s) / 12 h / -40 - 20 °C

2.3: H₂O

3.1: 82 percent / p-TsOH / CH₂Cl₂ / 2 h / 20 °C

4.1: 90 percent / Bu₄NF / tetrahydrofuran / 12 h / 20 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/b111071n

upstream raw materials:

(2S,4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-[(Z)-2-(tert-butyl-dimethyl-silanyl)-pentadec-1-enyl]-2-phenyl-[1,3]dioxane

Phenyl 2,3,4-tris-O-(tert-butyldimethylsilyl)-1-thio-β-D-xylopyranoside

Downstream raw materials:

(2R,3R)-trans-2-azide-1,3-O-benzylidene-1,3-octadec-4-enediol

2-azido-sphingosine

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol