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Di-sym-collidine Perchlorate

Synthetic Organic Reactions, 2nd ed. Benjamin Menlo Park, 1972 Chapter 9. [Pg.232]

Greene, T. W. Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed. Wiley New York, 1991 Chapter 2. [Pg.232]

Advanced Organic Chemistry, 3rd. ed. Wiley New York, 1985 p 799. [Pg.232]

Gary A. Sulikowski Michelle M. Sulikowski Texas A M University, College Station, TX, USA [Pg.232]

Form Supplied in fine colorless crystalline powder. [Pg.232]

Scheme 5.1 Mechanism of thioglycoside activation (a) by thiophiles X1 such as /V-bromosuccinimicle (NBS), 11,12 methyl triflate,13 dimethyl(methylthio)sulfonium triflate (DMTST),14 phenylselenyl triflate (PhSeOTf),17,18 iV-iodosuccinimide/triflic acid (MS/TfOH),19 20 and iodonium di-sym-collidine perchlorate (IDCP)21 (b) by tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA,+)25 and (c) via anomeric sulfoxides.26 The stereochemical outcome of these glycosylations follows the same general trends as with many other glycosyl donor/promoter combinations (m-CPBA = mcta-chloroperbenzoic acid). Scheme 5.1 Mechanism of thioglycoside activation (a) by thiophiles X1 such as /V-bromosuccinimicle (NBS), 11,12 methyl triflate,13 dimethyl(methylthio)sulfonium triflate (DMTST),14 phenylselenyl triflate (PhSeOTf),17,18 iV-iodosuccinimide/triflic acid (MS/TfOH),19 20 and iodonium di-sym-collidine perchlorate (IDCP)21 (b) by tris(4-bromophenyl)ammoniumyl hexachloroantimonate (TBPA,+)25 and (c) via anomeric sulfoxides.26 The stereochemical outcome of these glycosylations follows the same general trends as with many other glycosyl donor/promoter combinations (m-CPBA = mcta-chloroperbenzoic acid).
Scheme 5.7 (a) Mechanism of the w-pentenyl glycoside-based glycosylation method. Electrophiles commonly employed include iodonium di-sym-collidine perchlorate (IDCP) and A-iodosuccinimide/triethylsilyl triflate (NIS/Et3SiOTf) (b) Mechanism for the activation of NIS by EtsSiOTf.55... [Pg.107]

GLYCOSIDES Bromotrimcthyisilanc-Cobalt(II) bromide, lodonium di-sym-collidine perchlorate. Mercury(Il) nitrate. Silver imidazolale. Siannous chloride-Silver perchlorate. [Pg.474]

Lemieux and Thiem developed the iodine glycosylation.16 You need an I+-reagent e. g. Y-iodosuccinimide (l-iodo-2,5-pyrrolidinedione, NIS) (47) or I(coll)2 (iodonium di-.sym-collidine perchlorate) (48). The mechanism of this step with the bromine reagent of 48 was evaluated by Brown. 1... [Pg.276]

Bis(syfn-collidine)iodine(I) perchlorate (Iodonium di-sym-collidine) perchlorate, +I(C8H N)2 C104 (1), 10, 212-213. [Pg.30]

SESCl in Synthesis. The SES group has been used successfully in the synthesis of glycosides (eq 5). Reaction of (6) with SES-sulfonamide and iodonium di-sym-collidine perchlorate provides the iodo sulfonamide (7) in 82% yield. Treatment of (7) with (benzyloxy)trihutylstannane in the presence of silver(I) tri-fluoromethanesulfonate provides the /3-benzyl glycoside (8). Ru-oride treatment of (8) removes both the silyl ether and the SES group, giving the amino alcohol (9). [Pg.611]

Drying see Bromonium Di-sym-coUidine Perchlorate. Handling, Storage, and Precautions see Bromonium Di-sym-collidine Perchlorate. [Pg.232]

See other pages where Di-sym-collidine Perchlorate is mentioned: [Pg.143]    [Pg.474]    [Pg.474]    [Pg.313]    [Pg.477]    [Pg.222]    [Pg.173]    [Pg.526]    [Pg.526]    [Pg.253]    [Pg.241]    [Pg.241]    [Pg.43]    [Pg.46]    [Pg.27]    [Pg.451]    [Pg.117]    [Pg.232]    [Pg.233]    [Pg.488]    [Pg.497]   


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