2,3,4,6-tetra-O-benzyl-D-galactonamide

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-D-galactonamide
• CAS No.: 158349-18-9
• Molecular Formula: C₃₄H₃₇NO₆
• Molecular Weight: 555.671
• Mol file: 158349-18-9.mol

Synonyms:2,3,4,6-tetra-O-benzyl-D-galactonamide

Chemical Property of 2,3,4,6-tetra-O-benzyl-D-galactonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4,6-tetra-O-benzyl-D-galactonamide

There total 6 articles about 2,3,4,6-tetra-O-benzyl-D-galactonamide 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: 100.0%

2,3,4,6-tetra-O-benzyl-D-galactonolactone (82598-84-3) → 2,3,4,6-tetra-O-benzyl-D-galactonamide (158349-18-9)

Guidance literature:

With ammonia; In methanol;

DOI:10.1016/S0040-4039(03)00512-4

Reference yield: 85.0%

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) → 2,3,4,6-tetra-O-benzyl-D-galactonamide (158349-18-9)

Guidance literature:

With ammonium hydroxide; iodine; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/jccs.200300018

Reference yield:

allyl D-galactopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0) → 2,3,4,6-tetra-O-benzyl-D-galactonamide (158349-18-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: 7 h / 20 °C / Inert atmosphere

2.1: potassium tert-butylate / N,N-dimethyl-formamide / 2 h / 70 °C / Inert atmosphere

2.2: 0.08 h / Cooling; Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: ammonia / methanol / 1 h / 20 °C / Inert atmosphere

With potassium tert-butylate; ammonia; sodium hydride; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1016/j.tetlet.2013.03.083

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-galactonolactone

2,3,4,6-tetra-O-benzyl-D-galactopyranose

acetic anhydride

D-Galactose

Downstream raw materials:

3,5-dibenzyloxy-6-benzyloxymethyl-2-pyridone

5-hydroxy-2,3,4,6-tetra-O-benzyl-δ-lactam

(3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)piperidin-2-one

2-Nitro-N-((2S,3R,4S,5R)-2,3,4,6-tetrakis-benzyloxy-5-hydroxy-hexyl)-benzenesulfonamide

Refernces

• 1、 Kanso, Rami,Striegler, Susanne. "Multi gram-scale synthesis of galactothionolactam and its transformation into a galactonoamidine". scheme or table. p. 897 - 904. Retrieved 2011/06/19.
• 2、 Chen, Ming-Yi,Hsu, Jue-Liang,Shie, Jiun-Jie,Fang, Jim-Min. "Direct oxidative amidation of aldoses by iodine in ammonia water". . p. 129 - 133. Retrieved 2007/10/03.