4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, monohydrochloride, 3aR-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-

Base Information

• Chemical Name: 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, monohydrochloride, 3aR-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-
• CAS No.: 114673-96-0
• Molecular Formula: C₉H₁₆N₂O₄*ClH
• Molecular Weight: 252.698
• Mol file: 114673-96-0.mol

Synonyms:4H-Cyclopentoxazole-4,5-diol,2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, monohydrochloride,[3aR-(3aa,4a,5b,6a,6aa)]- (9CI); (-)-Allosamizoline hydrochloride;Allosamizoline hydrochloride

Chemical Property of 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, monohydrochloride, 3aR-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-

Chemical Property:

• PSA: 85.52000
• LogP: -1.74710

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, monohydrochloride, 3aR-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)-

There total 45 articles about 4H-Cyclopentoxazole-4,5-diol, 2-(dimethylamino)-3a,5,6,6a-tetrahydro-6-(hydroxymethyl)-, monohydrochloride, 3aR-(3a.alpha.,4.alpha.,5.beta.,6.alpha.,6a.alpha.)- 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: 98.0%

3,4,6-tri-O-acetylallosamizoline (114621-71-5) → (-)-allosamizoline hydrochloride (114673-96-0)

Guidance literature:

With hydrogenchloride; sodium methylate; In methanol; 1) RT, overnight;

Reference yield:

3-O-benzylallosamizoline (252055-28-0) → (-)-allosamizoline hydrochloride (114673-96-0)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In water; Yield given;

DOI:10.1016/S0040-4039(00)93444-0

Reference yield:

2-amino-4,6-O-benzylidene-3-O-(N-propylcarbamoyl)-2-deoxy-α-D-glucopyranoside (99679-74-0) → (-)-allosamizoline hydrochloride (114673-96-0)

Guidance literature:

Multi-step reaction with 15 steps

1: BaO, Ba(OH)2 / dimethylformamide

2: KOH, MeOC₂H₄OH / methanol; dioxane

3: NEt₃ / CH₂Cl₂

4: aq. AcOH

5: N-iodosuccinimide, PPh₃ / tetrahydrofuran

6: 2,6-lutidine / CH₂Cl₂

7: 96 percent / t-BuOK / tetrahydrofuran

8: 1) HgSO₄, 5M H₂SO₄, 2) MsCl, pyridine / 1) acetone, 60 deg C

9: NaBH₄, CeCl₃*7H₂O / methanol

10: Ms₂O, NEt₃ / methanol / CH₂Cl₂

11: 92 percent / OsO₄, Me₃N->O / H₂O; 2-methyl-propan-2-ol

12: 86 percent / DMAP, pyridine / CH₂Cl₂

13: 86 percent / L-Selectride / tetrahydrofuran / 65 °C

14: 1M HCl / H₂O; tetrahydrofuran

15: H₂, 1M HCl / 10percent Pd/C / H₂O

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; barium dihydroxide; potassium hydroxide; sodium tetrahydroborate; N-iodo-succinimide; osmium(VIII) oxide; cerium(III) chloride; 2-methoxy-ethanol; trimethylamine-N-oxide; sulfuric acid; potassium tert-butylate; hydrogen; L-Selectride; mercury(II) sulfate; acetic acid; methanesulfonyl chloride; triethylamine; triphenylphosphine; barium(II) oxide; Methanesulfonic anhydride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)93444-0

upstream raw materials:

3-O-benzylallosamizoline

3,4,6-tri-O-acetylallosamizoline

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(benzyloxycarbonyl)amino-α/β-D-glucopyranoside

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose