Trichloro(prop-2-en-1-yl)stannane

Base Information

• Chemical Name: Trichloro(prop-2-en-1-yl)stannane
• CAS No.: 65317-09-1
• Molecular Formula: C3H5Cl3Sn
• Molecular Weight: 266.142
• DSSTox Substance ID: DTXSID20578913
• Wikidata: Q82469259

Synonyms:Trichloro(prop-2-en-1-yl)stannane;Allyltrichlorostannane;65317-09-1;SCHEMBL387490;RCLQTMSHKBQDLK-UHFFFAOYSA-;DTXSID20578913

Chemical Property of Trichloro(prop-2-en-1-yl)stannane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 265.847886
• Heavy Atom Count: 7
• Complexity: 65.1

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC[Sn](Cl)(Cl)Cl

Technology Process of Trichloro(prop-2-en-1-yl)stannane

There total 6 articles about Trichloro(prop-2-en-1-yl)stannane 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:

2((CH3)3CCHO)*SnCl4 + trimethyl(allyl)stannane (762-73-2) + tin(IV) chloride (7646-78-8) → trimethyltin(IV)chloride (1066-45-1) + 2-propenyltrichlorostannane (65317-09-1)

Guidance literature:

In chloroform-d1; dichloromethane-d2; 0.5 M CDCl3/CD2Cl2 (1:1) at -80°C; (13)C-NMR;

DOI:10.1021/ja00211a058

Reference yield:

trimethyl(allyl)stannane (762-73-2) + tin(IV) chloride (7646-78-8) → trimethyltin(IV)chloride (1066-45-1) + 2-propenyltrichlorostannane (65317-09-1)

Guidance literature:

In chloroform-d1; dichloromethane-d2; CDCl3/CD2Cl2 = 1:1 at 0.5 M, metathesis is instantaneous and quant. at -80°C; (13)C-NMR;

DOI:10.1021/ja00211a058

Reference yield:

tetraallyl tin (7393-43-3) + tin(IV) chloride (7646-78-8) → trimethyltin(IV)chloride (1066-45-1) + 2-propenyltrichlorostannane (65317-09-1)

Guidance literature:

In chloroform-d1; dichloromethane-d2; CDCl3/CD2Cl2 = 1:1, 0.5 M, metathesis is instantaneous and quant. at -80°C; (13)C-NMR;

DOI:10.1021/ja00211a058

upstream raw materials:

trimethyl(allyl)stannane

tin(IV) chloride

4-tert-Butylbenzaldehyde

tetraallyl tin

Downstream raw materials:

(3R,4S)-4-[(S)-2,2-dimethyl-1,3-dioxolanyl-4-yl]-3-hydroxy-1-(p-methoxyphenyl)-3-(2-propenyl)-2-azetidinone

butyl (2S)-2-<(R)-1-phenylethylamino>pent-4-enoate

butyl (2R)-2-<(R)-1-phenylethylamino>pent-4-enoate

Refernces

Allyltrichlorostannane additions to α-amino aldehydes: Application to the total synthesis of the aspartyl protease inhibitors L-682,679, L-684,414, L-685,434, and L-685,458

10.1055/s-2003-37649

The research focuses on the total synthesis of aspartyl protease inhibitors, specifically L-682,679, L-684,414, L-685,434, and L-685,458, which are hydroxyethylene dipeptide isosteres. These compounds are of significant interest due to their potential as inhibitors of aspartyl proteases, enzymes implicated in diseases such as HIV and Alzheimer's. The synthetic approach involves an allyltrichlorostannane coupling with α-amino aldehydes, followed by hydroboration, lactonization under TPAP conditions, lactone opening, and peptide coupling with the desired amine or dipeptide amide. The purpose of this research is to develop a practical and efficient synthetic method for these inhibitors, which could lead to a wide range of other dipeptide isosteres. The conclusions drawn from the research indicate that the synthetic methodology is effective and provides a foundation for further biological studies and the development of novel analogues. Key chemicals used in the process include allyltrichlorostannane, α-amino aldehydes, hydroxyethylene dipeptide isosteres, and various reagents for the peptide coupling and protection/deprotection steps.

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