5-Iodo-A-85380, 5-trimethylstannyl N-boc derivative

Base Information

• Chemical Name: 5-Iodo-A-85380, 5-trimethylstannyl N-boc derivative
• CAS No.: 213766-21-3
• Molecular Formula: C₁₇H₂₈N₂O₃Sn
• Molecular Weight: 427.131
• DSSTox Substance ID: DTXSID20441936
• Wikidata: Q82258946
• Mol file: 213766-21-3.mol

Synonyms:213766-21-3;5-IODO-A-85380, 5-TRIMETHYLSTANNYL N-BOC DERIVATIVE;Tert-butyl (2S)-2-[(5-trimethylstannylpyridin-3-yl)oxymethyl]azetidine-1-carboxylate;(2S)-2-[[[5-(Trimethylstannyl)-3-pyridinyl]oxy]methyl]-1-azetidinecarboxylicacid,t-butylester;SCHEMBL3358315;DTXSID20441936;AKOS024456649;NCGC00162455-01;PD071017;J-014019;5-Iodo-a-85380,5-trimethylstannyl N-boc derivative;3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5(trimethylstannyl)pyridine;3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine;(2S)-2-[[[5-(Trimethylstannyl)-3-pyridinyl]oxy]methyl]-1-azetidinecarboxylic acid, t-butyl ester

Chemical Property of 5-Iodo-A-85380, 5-trimethylstannyl N-boc derivative

Chemical Property:

• PSA: 51.66000
• LogP: 2.95290
• Storage Temp.: Desiccate at -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 428.112195
• Heavy Atom Count: 23
• Complexity: 417

Purity/Quality:

98%min ^*data from raw suppliers

5-Iodo-A-85380, 5-trimethylstannyl N-BOC derivative ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC1COC2=CC(=CN=C2)[Sn](C)(C)C
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@H]1COC2=CC(=CN=C2)[Sn](C)(C)C
• Uses: 5-Iodo-A-85380, 5-Trimethylstannyl N-BOC Derivative is a precursor to the highly potent and selective ligand for AChR α4β2, 5-Iodo-A-85380. It is suitable for radioiodination.

Technology Process of 5-Iodo-A-85380, 5-trimethylstannyl N-boc derivative

There total 3 articles about 5-Iodo-A-85380, 5-trimethylstannyl N-boc derivative 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: 90.0%

hexamethyldistannane (661-69-8) + (S)-2-(5-bromo-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester (186593-31-7) → tert-butyl (2S)-2-({[5-(trimethylstannyl)pyridin-3-yl]oxy}methyl)azetidine-1-carboxylate (213766-21-3)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 27h;

Reference yield: 37.0%

(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate (228867-09-2) + hexamethyldistannane (661-69-8) → 3-[[1-(tert-butoxycarbonyl)-2(R)-azetidinyl]methoxy]-5-(trimethylstannyl)pyridine (1222138-49-9,213766-21-3)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; at 90 ℃; for 26h;

Reference yield:

5-bromopyridine-3-ol (74115-13-2) → tert-butyl (2S)-2-({[5-(trimethylstannyl)pyridin-3-yl]oxy}methyl)azetidine-1-carboxylate (213766-21-3)

Guidance literature:

Multi-step reaction with 2 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran; toluene / 0.5 h / Cooling with ice; Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 27 h / 90 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; toluene;

upstream raw materials:

hexamethyldistannane

(S)-2-(5-bromo-pyridin-3-yloxymethyl)-azetidine-1-carboxylic acid tert-butyl ester

5-bromopyridine-3-ol

(R)-tert-butyl 2-((5-bromopyridin-3-yloxy)methyl)azetidine-1-carboxylate

Downstream raw materials:

3-[4-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]-1-propanol

N-[3-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]propyl]-3,4,5,6-tetrachlorophthalimide

3-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]propanamine

N-[3-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]propyl]acetamide