81616-13-9

Basic information

• Product Name: <<β-(trimethylsilyl)ethoxy>carbonyl>benzylamine
• Synonyms: <<β-(trimethylsilyl)ethoxy>carbonyl>benzylamine
• CAS NO: 81616-13-9
• Molecular Weight: 251.401
• Mol File: 81616-13-9.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: <<β-(trimethylsilyl)ethoxy>carbonyl>benzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: <<β-(trimethylsilyl)ethoxy>carbonyl>benzylamine(81616-13-9)
• EPA Substance Registry System: <<β-(trimethylsilyl)ethoxy>carbonyl>benzylamine(81616-13-9)

Safety Data

• Hazardous Substances Data: 81616-13-9(Hazardous Substances Data)

Upstream product

• 1001067-09-9 2-(trimethylsilyl)ethyl 3-nitro-1H-1,2,4-triazole-1-carboxylate 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 100-46-9 benzylamine 
• 20160-60-5 2-(trimethylsilyl)-ethoxycarbonyl chloride 
• 103-82-2 phenylacetic acid 
• 81616-12-8 (β-trimethylsilyl)ethyl α-methoxyvinyl carbonate 

Relevant articles and documents

Unified Total Synthesis of Madangamine Alkaloids

The full details of a unified total synthesis of madangamine alkaloids are disclosed. Our central strategy is based on the construction of a common ABCE-tetracyclic system, followed by the late-stage installation of various D-rings. The common intermediate is assembled through N-acyliminium cyclization of a propargylsilane, and formation of the (Z,Z)-skipped diene. Stereoselective synthesis of the (Z,Z)-skipped diene is especially challenging, and is accomplished by the combination of Z-selective hydroboration of the 1,1-disubstituted allene and subsequent Migita-Kosugi-Stille coupling. Macrocyclic alkylation enables the late-stage variation of the D-rings on the common tetracyclic intermediate, resulting in the collective total syntheses of madangamines AE. The synthetic madangamine alkaloids exhibited inhibitory activities against a variety of human cancer cell lines.

Unified Total Synthesis of Madangamines A, C, and E

A stereodivergent strategy for the synthesis of skipped dienes is developed. The method consists of hydroboration of allenes and Migita-Kosugi-Stille coupling, which allows for access to all four possible stereoisomers of the skipped dienes. The hydroboration is especially useful for providing both E-allylic and Z-allylic alcohols from the same allene by simply changing the organoborane reagent. The strategy was successfully applied to a unified total synthesis of the madangamine alkaloids via a common ABCE-tetracyclic intermediate with a (Z,Z)-skipped diene. The late-stage variation of the D-ring enabled the supply of synthetic madangamines A, C, and E for the first time.

Amino-Protecting Reagents: New Promising Reagents for tert-Butoxycarbonylation, Benzyloxycarbonylation, and carbonylation

A new method for the preparation of tert-butyl- (1d), benzyl- (1e), and (β-trimethylsilyl)ethyl α-methoxyvinyl carbonates (1f) has been devised.The reaction of these reagents with amino compounds proceeds rapidly under mild conditions to give the corresponding N-tert-butoxycarbonylated (N-Boc), N-benzyloxycarbonylated (N-Z), and N-carbonylated (N-Tmseoc) compounds in quantitative yields.Twenty-two examples using amines, amino alcohols, and amino acids were presented.