The selective distinction of diethylisopropylsilyl ether in hydrogenolysis

Toshima, Kazunobu; Yanagawa, Koji; Mukaiyama, Satsuki; Tatsuta, Kuniaki

doi:10.1016/s0040-4039(00)97150-8

Cited by 30 publications

(6 citation statements)

References 6 publications

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“…The isoxazoline opening was achieved by reduction of 144 with Raney Ni-W4 in the presence of AcOH to afford the keto-diol, which was silylated with diethylisopropylsilyl triflate to give the protected ketone 145 . The diethylisopropylsilyl (DEIPS) group was developed in our laboratories and effectively used as an O -protecting group, 52 ) because this silyl group was found to be readily removed under hydrogenolysis conditions using Pd(OH) 2 . The mesylate 146 was subjected to hydrogenolysis followed by epoxidation to give cyclophellitol ( 147 ), thereby completing the first total synthesis.…”

Section: Total Syntheses Of Useful Glycosidase Inhibitors and Synthetmentioning

confidence: 99%

Total synthesis and development of bioactive natural products

Tatsuta

2008

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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The first total synthesis and development of a variety of bioactive natural products have been accomplished by using carbohydrates as a chiral source. In addition, practically useful intermediates have been created, analogs of natural products have been prepared, their structure-activity relationships studied, and the large-scale preparations of medicinally useful compounds established. The key target molecules have been the “Big Four” antibiotics (macrolides, aminoglycosides, β-lactams and tetracyclines), pyranonaphthoquinone antibiotics, glycosidase inhibitors, and a side-chain of cephem antibiotics.

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Section: Total Syntheses Of Useful Glycosidase Inhibitors and Synthetmentioning

confidence: 99%

Total synthesis and development of bioactive natural products

Tatsuta

2008

Proceedings of the Japan Academy. Ser. B: Physical and Biologic

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“…This fact has been utilized in the synthesis of the unstable elaiophylin [188]. In addition, it has been found that, although the DEIPS and benzyl groups are removed without affecting the TBDPS group under hydrogenolysis conditions using Pd(OHh in MeOH (reactionas 1 and 2 in Scheme 64) [189,190], benzyl ethers are selectively cleaved in p-dioxane with retention of the DEIPS groups (reaction 3 in Scheme 64) [189].…”

Section: Oiethylisopropylsilyl (Oeips) Groupmentioning

confidence: 99%

Reactions at Oxygen Atoms

Tsuchiya¹

2001

Glycoscience: Chemistry and Chemical Biology I–III

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“…In fact, it has previously been reported in the literature that primary and secondary silyl-protected alcohols such as the TBS and DEIPS ethers could be cleaved using various hydrogenolysis conditions [Pd(OH) 2 , wet Pd/C, catalytic transfer hydrogenation]. Smith et al had also noticed, during their synthesis of (+)-phyllanthoside, that it was necessary to carefully monitor hydrogenolysis of the benzyl ethers using 10% Pd/C in freshly distilled ethyl acetate to minimize deprotection of the silyl ethers …”

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confidence: 99%