(4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione

Base Information

• Chemical Name: (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione
• CAS No.: 206655-90-5
• Molecular Formula: C₂₄H₃₀N₂O₄S
• Molecular Weight: 442.579
• Mol file: 206655-90-5.mol

Synonyms:(4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione

Chemical Property of (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione

There total 5 articles about (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione 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%

carbon disulfide (75-15-0,12122-00-8) + 1,6-dianino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-L-iditol (206655-89-2) → (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione (206655-90-5)

Guidance literature:

In pyridine; at 60 ℃; for 15h;

DOI:10.1016/S0968-0896(99)00294-1

Reference yield:

1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-L-iditol (111651-40-2) → (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione (206655-90-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / tetrahydrofuran / 3 h / 20 °C

1.2: 77 percent / 15 h / 20 °C

2.1: 70 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C

3.1: 100 percent / pyridine / 15 h / 60 °C

With hydrogen; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; 1.1: Metallation / 1.2: Substitution / 2.1: Reduction / 3.1: Cycloaddition;

DOI:10.1016/S0968-0896(99)00294-1

Reference yield:

1,6-diazido-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-L-iditol (206655-88-1) → (4S,5R,6R,7S)-5,8-dibenzyloxymethyl-6,7-dihydroxy-6,7-O-methylethylidene-1,3-diazepan-2-thione (206655-90-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / H₂ / Pd/C / ethanol / 2 h / 20 °C

2: 100 percent / pyridine / 15 h / 60 °C

With hydrogen; palladium on activated charcoal; In pyridine; ethanol; 1: Reduction / 2: Cycloaddition;

DOI:10.1016/S0968-0896(99)00294-1

upstream raw materials:

carbon disulfide

1,6-dianino-2,5-di-O-benzyl-1,6-dideoxy-3,4-O-methylethylidene-L-iditol

benzyl bromide

1,6-diazido-1,6-dideoxy-3,4-O-methylethylidene-L-iditol

Downstream raw materials:

(5S,6R,7R,8S)-5,8-dibenzyloxy-6,7-dihydroxy-6,7-O-methylethylidene-2-(N-benzyl)-imino-1,3-diazonane