4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam

Base Information

• Chemical Name: 4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam
• CAS No.: 911386-19-1
• Molecular Formula: C₂₄H₂₇NO₆S
• Molecular Weight: 457.547

Synonyms:4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam

Chemical Property of 4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam

Chemical Property:

Purity/Quality:

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Technology Process of 4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam

There total 2 articles about 4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam 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%

4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-lactam (911386-18-0) → 4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam (911386-19-1)

Guidance literature:

With Lawessons reagent; In toluene; at 80 ℃; for 0.5h;

DOI:10.1002/hlca.200690137

Reference yield:

5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-lactam (896447-96-4) → 4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam (911386-19-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / pyridine / 6 h / 0 °C

2: 85 percent / Lawesson's reagent / toluene / 0.5 h / 80 °C

With Lawessons reagent; pyridine; In toluene;

DOI:10.1002/hlca.200690137

Reference yield:

4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-thiolactam (911386-19-1) + 2,2-dimethoxyethylamine (22483-09-6) → Acetic acid (2R,3S,4S,5S)-2-acetoxymethyl-4,5-bis-benzyloxy-6-[(Z)-2,2-dimethoxy-ethylimino]-piperidin-3-yl ester

Guidance literature:

With mercury(II) diacetate; In tetrahydrofuran; at 0 ℃; for 2h;

DOI:10.1002/hlca.200690137

upstream raw materials:

4,6-di-O-acetyl-5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-lactam

5-amino-2,3-di-O-benzyl-5-deoxy-D-galactono-1,5-lactam

Downstream raw materials:

(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-5-methanol

(5R,6S,7S,8S)-7,8-bis(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-6-ol

(5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5-{[(tert-butyl)dimethylsilyloxy]methyl}-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine

diphenylmethyl (5R,6S,7S,8S)-6,7,8-tris(benzyloxy)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-5-carboxylate

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