[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine

Base Information

• Chemical Name: [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine
• CAS No.: 158226-48-3
• Molecular Formula: C₂₉H₄₂N₂O₄Si
• Molecular Weight: 510.749
• Mol file: 158226-48-3.mol

Synonyms:[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine

Chemical Property of [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine

There total 1 articles about [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine 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:

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol (139573-30-1) → [(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine (158226-48-3)

Guidance literature:

With trifluorormethanesulfonic acid; In hexane; dichloromethane;

DOI:10.1016/S0040-4039(00)60825-0

Reference yield: 60.0%

[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine (158226-48-3) → (1S,2S,3R,4R,5S)-2-Amino-3-benzyloxy-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol (158226-49-4)

Guidance literature:

With hydrazine hydrate; In ethanol; at 80 ℃; for 8h;

DOI:10.1016/S0040-4039(00)73136-4

Reference yield:

[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-2-yl]-dimethyl-amine (158226-48-3) → allosamidin (144539-85-5,103782-08-7,153322-50-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1M HCl / tetrahydrofuran

2: 40 percent / N-iodosuccinimide, TfOH / CH₂Cl₂ / 0 °C / molecular sieves 4 Angstroem

3: aq. methylamine / ethanol

4: methanol

5: H₂ / Pd-C / acetic acid; methanol; H₂O

With hydrogenchloride; N-iodo-succinimide; trifluorormethanesulfonic acid; hydrogen; methylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetic acid;

DOI:10.1016/S0040-4039(00)60825-0

upstream raw materials:

O-benzyl 2,2,2-trichloroacetimidate

[(3aS,4R,5R,6S,6aS)-4-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-dimethylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-6-yl]-methanol

Downstream raw materials:

3,6-di-O-benzyl-(-)-allosamizoline

(1S,2S,3R,4R,5S)-2-Amino-3-benzyloxy-5-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclopentanol

(3aS,4R,5R,6R,6aS)-4-Benzyloxy-6-benzyloxymethyl-2-methylamino-4,5,6,6a-tetrahydro-3aH-cyclopentaoxazol-5-ol

1-[(1S,2R,3R,4S,5S)-2-Benzyloxy-4-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-cyclopentyl]-3-methyl-thiourea