N-(1,7,8-Trihydroxyoctahydroindolizin-6-yl)acetamide

Base Information

• Chemical Name: N-(1,7,8-Trihydroxyoctahydroindolizin-6-yl)acetamide
• CAS No.: 134100-29-1
• Molecular Formula: C10H18N2O4
• Molecular Weight: 230.26
• DSSTox Substance ID: DTXSID30601620
• Mol file: 134100-29-1.mol

Synonyms:N-(1,7,8-Trihydroxyoctahydroindolizin-6-yl)acetamide;N-(1,7,8-trihydroxy-1,2,3,5,6,7,8,8a-octahydroindolizin-6-yl)acetamide;DTXSID30601620

Chemical Property of N-(1,7,8-Trihydroxyoctahydroindolizin-6-yl)acetamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• Boiling Point: 528.7°Cat760mmHg
• Flash Point: 273.5°C
• PSA: 93.03000
• Density: 1.4g/cm³
• LogP: -2.00950
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 230.12665706
• Heavy Atom Count: 16
• Complexity: 286

Purity/Quality:

≥95% ^*data from raw suppliers

6-Acetamido-6-deoxycastanospermine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1CN2CCC(C2C(C1O)O)O
• Uses: hexosaminidase inhibitor

Technology Process of N-(1,7,8-Trihydroxyoctahydroindolizin-6-yl)acetamide

There total 19 articles about N-(1,7,8-Trihydroxyoctahydroindolizin-6-yl)acetamide 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%

6-acetamido-1,7,8-tri-O-acetyl-6-deoxycastanospermine (156205-53-7) → 6-acetamido-6-deoxycastanospermine (134100-29-1)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1016/S0040-4020(01)85075-4

Reference yield: 83.0%

[1S-(1α,6β,7α,8β,8aβ)]-6-azidooctahydro-1,7,8-indolizinetriol 1,8-diacetate 7-benzoate → 6-acetamido-6-deoxycastanospermine (134100-29-1)

Guidance literature:

With sodium methylate; palladium-carbon; In methanol; water;

Reference yield:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) → 6-acetamido-6-deoxycastanospermine (134100-29-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / pyridine / 0 deg C -> r.t., overnight

2: 30 percent / tributyltin methoxide / tetrahydrofuran / Heating

3: 86 percent / pyridine

4: 56 percent / NaN₃ / dimethylsulfoxide / 80 deg C, 1 h; 60 deg C, overnight

5: 81 percent / H₂ / 5percent Pd/C / toluene / 24 h

6: 101 percent / pyridine / Ambient temperature

7: 100 percent / NaOMe / methanol

With pyridine; sodium azide; hydrogen; sodium methylate; tributyltin methoxide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4020(01)85075-4

upstream raw materials:

acetic anhydride

6-amino-6-deoxycastanospermine

6-acetamido-1,7,8-tri-O-acetyl-6-deoxycastanospermine

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine