(S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one

Base Information

• Chemical Name: (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one
• CAS No.: 1287297-26-0
• Molecular Formula: C₃₇H₅₂ClNO₁₁
• Molecular Weight: 722.273
• Mol file: 1287297-26-0.mol

Synonyms:(S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one

Chemical Property of (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one

There total 2 articles about (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one 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:

(furan-2-yloxy)-trimethylsilane (61550-02-5) + C33H48ClNO9 (120255-31-4) → (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one (1287297-26-0) + (R)-5-((S)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one

Guidance literature:

With zinc chloride diethyl ether; In diethyl ether; at -78 ℃; for 12h; optical yield given as %de; Inert atmosphere;

DOI:10.1039/c0ob01048k

Reference yield:

4-chlorobenzaldehyde (104-88-1) + tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6) → (S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one (1287297-26-0) + (R)-5-((S)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one

Guidance literature:

Multi-step reaction with 2 steps

1: acetic acid / isopropyl alcohol / 0.5 h / 20 °C / Inert atmosphere

2: zinc chloride diethyl ether / diethyl ether / 12 h / -78 °C / Inert atmosphere

With zinc chloride diethyl ether; acetic acid; In diethyl ether; isopropyl alcohol; 2: Mannich type reaction;

DOI:10.1039/c0ob01048k

Reference yield: 100.0%

(S)-5-((R)-(2,2,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino(4-chlorophenyl)methyl)-5H-furan-2-one (1287297-26-0) → (S)-5-((R)-amino(4-chlorophenyl)methyl)furan-2(5H)-one hydrochloride

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 36h; Inert atmosphere;

DOI:10.1039/c0ob01048k

upstream raw materials:

(furan-2-yloxy)-trimethylsilane

C₃₃H₄₈ClNO₉

4-chlorobenzaldehyde

tetra-O-pivaloyl-β-D-galactopyranosylamine