(2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane

Base Information

• Chemical Name: (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane
• CAS No.: 349555-96-0
• Molecular Formula: C₃₅H₄₉NO₄Si
• Molecular Weight: 575.864
• Mol file: 349555-96-0.mol

Synonyms:(2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane

Chemical Property of (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane

There total 3 articles about (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane 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: 85.0%

benzyl bromide (100-39-0) + (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-5-[1,3]dioxolan-2-yl-pentan-3-ol (305838-42-0) → (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane (349555-96-0)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1016/S0040-4039(01)00483-X

Reference yield:

2-bromo-2-(2-ethyl)dioxolane (18742-02-4) → (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane (349555-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg / tetrahydrofuran / 1 h / 20 °C

1.2: 86 percent / tetrahydrofuran / 1 h / 20 °C

2.1: 85 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium; In tetrahydrofuran;

DOI:10.3987/COM-04-S(P)21

Reference yield:

(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde (125654-82-2) → (2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-3-benzyloxy-5-[1,3]dioxolan-2-yl-pentane (349555-96-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg / tetrahydrofuran / 1 h / 20 °C

1.2: 86 percent / tetrahydrofuran / 1 h / 20 °C

2.1: 85 percent / NaH; Bu₄NI / tetrahydrofuran / 12 h / 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium; In tetrahydrofuran;

DOI:10.3987/COM-04-S(P)21

upstream raw materials:

benzyl bromide

(2S,3R)-1-(tert-butyldimethylsilanyloxy)-2-dibenzylamino-5-[1,3]dioxolan-2-yl-pentan-3-ol

2-bromo-2-(2-ethyl)dioxolane

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

Downstream raw materials:

(4R,5S)-6-(tert-butyldimethylsilanyloxy)-4-benzyloxy-5-dibenzylaminohexanal

(2S,3R)-1-(tert-butyldimethylsilanyloxy)-3-benzyloxy-2-dibenzylaminooctadecane-1,6-diol

(2S,3R)-1-(tert-butyldimethylsilanyloxy)-3-benzyloxy-2-dibenzylamino-6-oxooctadecan-6-one

(2S,3R,6S)-(3-benzyloxy-6-dodecylpiperidin-2-yl)methanol