(2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

Base Information

• Chemical Name: (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester
• CAS No.: 518308-54-8
• Molecular Formula: C₃₁H₃₁NO₆S
• Molecular Weight: 545.656
• Mol file: 518308-54-8.mol

Synonyms:(2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

Chemical Property of (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

There total 7 articles about (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester 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: 91.0%

benzyloxyacetoaldehyde (60656-87-3) + Propionic acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester (518308-45-7) → (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester (518308-54-8)

Guidance literature:

With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; at -78 ℃; for 2h;

DOI:10.1021/ol034086n

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester (518308-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / DMAP; Et₃N / CH₂Cl₂; acetonitrile / 4 h / 0 °C

2: 95 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

3: 91 percent / TiCl₄; iPr₂NEt / CH₂Cl₂; acetonitrile / 2 h / -78 °C

With pyridine; dmap; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1021/ol034086n

Reference yield:

(1S,2R)-2-amino-1-acenaphthenol (161595-81-9) → (2R,3R)-4-Benzyloxy-3-hydroxy-2-methyl-butyric acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester (518308-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / DMAP; Et₃N / CH₂Cl₂; acetonitrile / 4 h / 0 °C

2: 95 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

3: 91 percent / TiCl₄; iPr₂NEt / CH₂Cl₂; acetonitrile / 2 h / -78 °C

With pyridine; dmap; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile;

DOI:10.1021/ol034086n

upstream raw materials:

benzyloxyacetoaldehyde

Propionic acid (1S,2R)-2-(toluene-4-sulfonylamino)-acenaphthen-1-yl ester

p-toluenesulfonyl chloride

(1S,2R)-2-amino-1-acenaphthenol

Downstream raw materials:

(2S,3R)-4-(benzyloxy)-2-methylbutane-1,3-diol

(4R,5S)-4-Benzyloxymethyl-2,2,5-trimethyl-[1,3]dioxane