1379039-08-3

Basic information

• Product Name: C₄₄H₅₃NO₃SSi₂
• Synonyms: C₄₄H₅₃NO₃SSi₂
• CAS NO: 1379039-08-3
• Molecular Weight: 732.147
• Mol File: 1379039-08-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₄₄H₅₃NO₃SSi₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₄H₅₃NO₃SSi₂(1379039-08-3)
• EPA Substance Registry System: C₄₄H₅₃NO₃SSi₂(1379039-08-3)

Safety Data

• Hazardous Substances Data: 1379039-08-3(Hazardous Substances Data)

Upstream product

• 1379039-05-0 N-p-toluenesulfonyl-4(R)-amino-5-tert-butyldiphenylsilyl-1-tert-butyldiphenylsilyloxy-2(S)-pentanol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 57850-05-2 (2S,4R)-2-Hydroxymethyl-4-hydroxy-1-(4-toluenesulfonyl)-pyrrolidine 

Relevant articles and documents

A smooth rearrangement of N-p-toluenesulfonyl 2-tert- butyldiphenylsilylmethyl-substituted azetidines into N-p-toluenesulfonyl 3-tert-butyldiphenylsilyl-substituted pyrrolidines

The rearrangement of N-p-toluenesulfonyl 2-tert-butyldiphenylsilylmethyl- substituted azetidines into 3-tert-butyldiphenylsilyl-substituted pyrrolidines under Lewis acid conditions in dichloromethane involves 1,2-migration of silicon through a siliranium ion. The formation of siliranium ion was discovered not to be in concert with σC-N cleavage from stereochemical analysis of the pyrrolidine products formed from 3- and 4-substituted-2-tert- butyldiphenylsilylmethyl azetidines and also from the optical rotation data and chiral HPLC analysis of the pyrrolidine product formed from N-p-toluenesulfonyl 2(R)-tert-butyldiphenylsilylmethyl azetidine. The formation of sterically less hindered siliranium ion is followed by its SN2 opening by the internal nitrogen nucleophile. Oxidative cleavage of σC-Si bond leads to the formation of 3-hydroxypyrrolidines.