CID 14636219

Base Information

• Chemical Name: CID 14636219
• CAS No.: 131635-62-6
• Molecular Formula: C₈H₁₄FNO₃
• Molecular Weight: 191.202
• Nikkaji Number: J377.032J
• Mol file: 131635-62-6.mol

Synonyms:131635-62-6;(1S,6S,7S,8R,8aR)-6-fluoro-1,2,3,5,6,7,8,8a-octahydroindolizine-1,7,8-triol;1,7,8-Indolizinetriol, 6-fluorooctahydro-, 1S-(1.alpha.,6.beta.,7.alpha.,8.beta.,8a.beta.)-;JOYRDAUHIQFEBO-TVNFTVLESA-N

Chemical Property of CID 14636219

Chemical Property:

• PSA: 63.93000
• LogP: -1.56700
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 191.09577147
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN2CC(C(C(C2C1O)O)O)F
• Isomeric SMILES: C1CN2C[C@@H]([C@H]([C@@H]([C@H]2[C@H]1O)O)O)F

Technology Process of CID 14636219

There total 8 articles about CID 14636219 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: 93.0%

(1S,6S,7S,8R,8aR)-8-(Benzyloxy)-6-fluoro-1,7-dihydroxyoctahydroindolizidine (131635-72-8) → (+)-6-deoxy-6-fluorocastanospermine (131635-62-6)

Guidance literature:

With formic acid; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 16h;

DOI:10.1039/c39900001070

Reference yield: 66.0%

1,7,8-tri-O-acetyl-6-deoxy-fluorocastenospermine (156205-45-7) → (+)-6-deoxy-6-fluorocastanospermine (131635-62-6)

Guidance literature:

With ammonia; In methanol; Ambient temperature;

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

Reference yield:

(1S,6R,7S,8R,8aR)-1,7-Diacetoxy-8-(benzyloxy)-6-fluorooctahydro-5-indolizidin-5-one (131635-71-7) → (+)-6-deoxy-6-fluorocastanospermine (131635-62-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) BH₃*Me₂S, 2) 3N HCl, MeOH / 1) THF, 20 deg C, 24 h, 2) 70 deg C, 4 h

2: 60 mg / H₂ / Pd/C / methanol; H₂O; formic acid / 20 °C / 760 Torr

With hydrogenchloride; methanol; dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In methanol; formic acid; water;

DOI:10.1021/jo00006a031

upstream raw materials:

(1S,6S,7S,8R,8aR)-8-(Benzyloxy)-6-fluoro-1,7-dihydroxyoctahydroindolizidine

1,7,8-tri-O-acetyl-6-deoxy-fluorocastenospermine

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

1,6,7,8-tetra-O-acetylcastanospermine