Scyllo

The 1-mesyloxy intermediate (6) was similarly prepared via the equatorial monobenzoate, and it reacted with azide ion by a single SN2 displacement, since no anchimeric effect was possible here. The scyllo... 

In early experiments, the pentamethyl ether (18) was treated with phosphorus pentachloride in the hope of obtaining a chloropentol reducible to ( — )-proto-quercitol. (Allowing for the benzoyl migration, the expected product would have been (— )-uibo-quercitol (11).) Surprisingly, the quercitol actually obtained after demethylation and dehalogena-tion was neither of these but still another previously known isomer, meso-scyllo-quercitol (24) (27). 

L. Sk0t and H. Egsgaard, Identification of ononitol and O-methyl-scyllo-inositol in pea root nodules. Plania 161 32-36 (1984). 

Scheme 66. Synthesis of scyllo-inositol repeating unit toward the construction of novel mannosylated...

Turner BL, Richardson AE. Identification of scyllo-inositol phosphates in soil by solution phosphorus-31 nuclear magnetic resonance spectroscopy. Soil Sci. Soc. Am. J. 2004 68 802-808. 

Scaffidi, A. and Stick, R.V., Glycosynthase-assisted synthesis of some glycosylated scyllo-inositols. Aust. J. Chem., 2006, 59, 894. 

SG7F10.16 StrB2 350 17123 scyllo -Inosamine-4-phosphate amidinotransferase... 

The General myo-lnositol and scyllo-Inosamine Pathway. Two distinct cyclitol pathways, which we earlier called Ca (started by myo-inositolphos-phate synthase) and Cb (started by T-deoxy-i cy/to-inosose synthase), are used in the initiation of AGA pathways. Here we will describe the Ca route and the Cb pathway in the paragraph on NEOs (see Section 2.2.2.1.3). The cyclitol pathway in the biosynthetic pathways for STRs, but also for other AGAs such as SPCs, KAS, and FORs and also the mixed type antibiotic HYG-A (see Section 2.2.4.3.1), starts with the formation of myo-inositol in a two-step pathway (Ca) that is not encoded in the itrAtt-clusters. The first step in streptidine biosynthesis (and any other myo-inositol utilising pathway) is the formation of a myo-inositol monophosphate (D-myo-inositol-3-phosphate or L-myo-inositol-1-phosphate) via L-myo-inositol-1-phosphate synthase, which in actinomycetes... 

SteO08.22c AprC 384 17039 2-Deoxy-scyllo -inosose synthase,cyclase... 

Lee and Ballou111 investigated five liquid phases for the separation of inositol trimethylsilyl ethers and concluded that QF-1 gave the best results. This column packing permitted resolution of all but the myo-cis pair of inositols. They reported that the order of appearance, regardless of the stationary phase used, is alio, (neo, muco), racemic, (scyllo, epi), and (myo, cis). The order within the parentheses is sometimes reversed, depending on the liquid phase used. Wells and co-... 

Hexa-0-(trimethylsilyl)-mj/o-inositol is a solid,112 and this compound and the crystalline per(trimethylsilyl) ethers of scyllo-inositol and myo-inosose-2 have been fully characterized by Loewus,407 who has proposed these compounds as suitable internal standards. The scyllo- and myo-inositols, together with myo-inosose-2, have also been used in a study on the use of electron-capture detectors with trimethylsilyl derivatives.579... 

M. Funabashi and J. Yoshimura, Branched chain sugars. Part 14. Synthesis of new branched-chain cyclitols having myo- or scyllo-, and muco-configuration from 3-< -benzyl-5,6-dideoxy-5-C-(l,3-dithian 2-yl)-6-nitro-L-idofuranose and D-glucofuranose, J. Chem. Soc. Perkin Trans, p. 1425 (1979). 

D. E. Kiely and H. G. Fletcher, Jr., Cyclization of D-xy(o-hexos-5-ulose, a chemical synthesis of scyllo- and myo-inositols from D-glucose, J. Org. Chem. 34 1386 (1969). 

Scheme 3.—Reactions of Radicals Derived from scyllo-Inositol. [The G-values of products77 in the y-radiolysis of a NjO-saturated, 0.01 M solution of scyllo-inositol at 0° and a dose rate of 2.9 W.kg-1 are G(scy//o-myo-inosose, 40) = 3.0, G(myo-inositol, 39) = 2.1, and G(deoxyinosose, 43) = 1.1].

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