Total synthesis of carbohydrates. 2. Regiochemical control of nucleophilic ring opening of acylated 2,3-epoxy alcohols

1983 ◽  
Vol 48 (25) ◽  
pp. 5083-5093 ◽  
Author(s):  
William R. Roush ◽  
Richard J. Brown ◽  
Marcello DiMare
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Epoxy Alcohols ◽  
Nucleophilic Ring Opening

Asymmetric total synthesis of paecilomycin C through intramolecular nucleophilic ring opening of an epoxide

2019 ◽  
Vol 17 (31) ◽  
pp. 7369-7379 ◽  
Author(s):  
Joy Chakraborty ◽  
Samik Nanda
Keyword(s):  
Total Synthesis ◽  
Ring Opening ◽  
Asymmetric Total Synthesis ◽  
Naturally Occurring ◽  
Acid Lactone ◽  
Nucleophilic Ring Opening

An efficient asymmetric total synthesis of naturally occurring resorcylic acid lactone (RAL) paecilomycin C was achieved by employing carboxylate assisted 5-exo-tet ring opening of an epoxide as a key reaction.

Eu(OTf)3-Catalyzed Highly Regioselective Nucleophilic Ring Opening of 2,3-Epoxy Alcohols: An Efficient Entry to 3-Substituted 1,2-Diol Derivatives

2014 ◽  
Vol 16 (17) ◽  
pp. 4408-4411 ◽  
Author(s):  
Shun-ichiro Uesugi ◽  
Tsubasa Watanabe ◽  
Takamichi Imaizumi ◽  
Masatoshi Shibuya ◽  
Naoki Kanoh ◽  
...  
Keyword(s):  
Ring Opening ◽  
Epoxy Alcohols ◽  
Nucleophilic Ring Opening

scholarly journals Synthesis of 3,3-Diaryl/Heteroarylpropylamines via Nucleophilic Ring Opening of Activated Azetidines with Arenes and Heteroarenes: New Synthetic Route to (±)Tolterodine

ACS Omega ◽  
2018 ◽  
Vol 3 (12) ◽  
pp. 17562-17572 ◽  
Author(s):  
Gaurav Goswami ◽  
Navya Chauhan ◽  
Abhijit Mal ◽  
Subhomoy Das ◽  
Mowpriya Das ◽  
...  
Keyword(s):  
Ring Opening ◽  
Synthetic Route ◽  
Nucleophilic Ring Opening

scholarly journals (1R,4S,5S)-5-((3-Hydroxypropyl)amino)-4-((1-Methyl-1H-tetrazol-5-yl)thio)Cyclopent-2-en-1-ol

Molbank ◽  
10.3390/m1199 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1199
Author(s):  
Milene A. G. Fortunato ◽  
Filipa Siopa ◽  
Carlos A. M. Afonso
Keyword(s):  
Spectral Data ◽  
13C Nmr ◽  
Ring Opening ◽  
Environmentally Friendly ◽  
Mass Spectral Data ◽  
Mass Spectral ◽  
Excellent Yield ◽  
Ring Opening Reaction ◽  
Nucleophilic Ring Opening

Using environmentally friendly conditions, the nucleophilic ring-opening reaction of 6-azabicyclo[3.1.0]hex-3-en-2-ol with 1-methyl-1H-tetrazole-5-thiol provided a novel thiol-incorporated aminocyclopentitol, (1R,4S,5S)-5-((3-hydroxypropyl)amino)-4-((1-methyl-1H-tetrazol-5-yl)thio)cyclopent-2-en-1-ol, in excellent yield (95%). The newly synthesized compound was analyzed and characterized via 1H, 13C-NMR, HSQC, and mass spectral data.

ChemInform Abstract: NEIGHBORING GROUP EFFECTS IN EPOXIDE RING OPENING, CIS-EPOXY-ALCOHOLS

1976 ◽  
Vol 7 (42) ◽  
pp. no-no
Author(s):  
ERWIN GLOTTER ◽  
PNINA KRINSKY ◽  
MIRIAM REJTOE ◽  
MARTIN WEISSENBERG
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Neighboring Group ◽  
Epoxide Ring Opening ◽  
Epoxy Alcohols ◽  
Group Effects
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