(2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal

Base Information

• Chemical Name: (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal
• CAS No.: 1438284-66-2
• Molecular Formula: C₃₉H₅₇NO₁₀
• Molecular Weight: 699.882
• Mol file: 1438284-66-2.mol

Synonyms:(2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal

Chemical Property of (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal

There total 2 articles about (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal 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:

1-(trimethylsiloxy)-1,3-butadiene (63383-46-0) + 2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester (202932-48-7) → (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal (1438284-50-4) + (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal (1438284-66-2)

Guidance literature:

With aluminum (III) chloride; In tetrahydrofuran; at -50 ℃; for 58h; Overall yield = 85 %; Overall yield = 178 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2013.03.020

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6) → (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal (1438284-50-4) + (2E,6E)-5-[(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)amino]-7-phenyl-hepta-2,6-dienal (1438284-66-2)

Guidance literature:

Multi-step reaction with 2 steps

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

2: aluminum (III) chloride / tetrahydrofuran / 58 h / -50 °C / Inert atmosphere

With aluminum (III) chloride; acetic acid; In tetrahydrofuran; isopropyl alcohol; 2: |Mannich Aminomethylation;

DOI:10.1016/j.carres.2013.03.020

upstream raw materials:

1-(trimethylsiloxy)-1,3-butadiene

2,2-Dimethyl-propionic acid (2R,3S,4S,5R,6R)-3,5-bis-(2,2-dimethyl-propionyloxy)-2-(2,2-dimethyl-propionyloxymethyl)-6-[(E)-3-phenyl-prop-2-en-(E)-ylideneamino]-tetrahydro-pyran-4-yl ester

(E)-3-phenylpropenal

tetra-O-pivaloyl-β-D-galactopyranosylamine