SCEPTRIN

Base Information

• Chemical Name: SCEPTRIN
• CAS No.: 79703-25-6
• Molecular Formula: C₂₂H₂₄Br₂N₁₀O₂*2ClH
• Molecular Weight: 693.228
• Mol file: 79703-25-6.mol

Synonyms:1H-Pyrrole-2-carboxamide,N,N'-[[(1R,2R,3S,4S)-3,4-bis(2-amino-1H-imidazol-4-yl)-1,2-cyclobutanediyl]bis(methylene)]bis[4-bromo-,dihydrochloride (9CI); 1H-Pyrrole-2-carboxamide,N,N'-[[3,4-bis(2-amino-1H-imidazol-4-yl)-1,2-cyclobutanediyl]bis(methylene)]bis[4-bromo-,dihydrochloride, [1R-(1a,2b,3a,4b)]-; (-)-Sceptrin dihydrochloride; Sceptrin; Sceptrin dihydrochloride;Sceptrine dihydrochloride

Chemical Property of SCEPTRIN

Chemical Property:

• PSA: 199.18000
• LogP: 6.00000
• Storage Temp.: −20°C

Purity/Quality:

95% ^*data from raw suppliers

SceptrinDihydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Sceptrin dihydrochloride is an antibiotic which inhibits cell motility.

Technology Process of SCEPTRIN

There total 13 articles about SCEPTRIN 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%

sceptrin acetate (117468-54-9) → (-)-sceptrin (79703-25-6)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00009a008

Reference yield:

dimethyl (1R,2R,3S,4S)-3,4-diacetylcyclobutane-1,2-dicarboxylate (878209-79-1) → (-)-sceptrin (79703-25-6)

Guidance literature:

Multi-step reaction with 11 steps

1: TsOH / methanol / 24 h / 50 °C

2: diisobutylaluminum hydride / CH₂Cl₂ / 1 h / -78 °C

3: pyridine / 1 h / 0 - 20 °C

4: sodium azide / dimethylformamide / 24 h / 50 °C

5: p-toluenesulfonic acid / methanol / 24 h / 50 °C

6: H₂ / Lindlar catalyst / methanol / 12 h / 23 °C / 760 Torr

7: acetonitrile / 4 h

8: benzyltrimethylammonium dichloroiodate / tetrahydrofuran / 1.75 h / 60 °C

9: acetonitrile / 40 h / 35 °C

10: aq. HCl / methanol / 16 h / 23 °C

11: H₂O / 4 h / 95 °C

With hydrogenchloride; sodium azide; hydrogen; diisobutylaluminium hydride; N,N,N-trimethylbenzenemethanaminium dichloroiodate; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja069035a

Reference yield:

1-(2-acetyl-3,4-bis-hydroxymethyl-cyclobutyl)-ethanone (936844-72-3) → (-)-sceptrin (79703-25-6)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 1 h / 0 - 20 °C

2: sodium azide / dimethylformamide / 24 h / 50 °C

3: p-toluenesulfonic acid / methanol / 24 h / 50 °C

4: H₂ / Lindlar catalyst / methanol / 12 h / 23 °C / 760 Torr

5: acetonitrile / 4 h

6: benzyltrimethylammonium dichloroiodate / tetrahydrofuran / 1.75 h / 60 °C

7: acetonitrile / 40 h / 35 °C

8: aq. HCl / methanol / 16 h / 23 °C

9: H₂O / 4 h / 95 °C

With hydrogenchloride; sodium azide; hydrogen; N,N,N-trimethylbenzenemethanaminium dichloroiodate; toluene-4-sulfonic acid; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja069035a

upstream raw materials:

sceptrin acetate

CYANAMID

dimethyl (1R,2R,3S,4S)-3,4-diacetylcyclobutane-1,2-dicarboxylate

1-(2-acetyl-3,4-bis-hydroxymethyl-cyclobutyl)-ethanone