C-Stannylated carbonydrate derivatives

Doidge-Harrison, Solange M.S.V.; Nowell, Ian W.; Cox, Philip; Howie, R. Α.; Taylor, O. J.; Wardell, James L.

doi:10.1016/0022-328x(91)86225-f

Cited by 19 publications

(6 citation statements)

References 19 publications

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“…These differ mostly by degree of distortion. Several derivatives contain two crystallographically independent molecules in the same crystal [50,67,75,79,80,82,84,88,93,95,100,110,117,123,124,140,142,168,175,176,187,189,191,197,212,213,218,221,225,245,253,258,270,289,298], In another two derivatives [31,168] three independent molecules are found, and three examples with four such molecules [160,166,204] in rH in rH 00 in CS rH CS CO CO CO CO rH rH CS CO rH CO rH CS <o rH rH -rH CS CS rH CO rH ΙΟ CS …”

Section: Structure Of Sn(ph) 3 (Mpo) [87a]mentioning

confidence: 98%

Tin Organometallic Compounds: Classification and Analysis of Crystallographic and Structural Data: Part 1. Monomeric Derivatives

Holloway¹,

Melnı́k²

2000

Main Group Metal Chemistry

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Section: Structure Of Sn(ph) 3 (Mpo) [87a]mentioning

confidence: 98%

Tin Organometallic Compounds: Classification and Analysis of Crystallographic and Structural Data: Part 1. Monomeric Derivatives

Holloway¹,

Melnı́k²

2000

Main Group Metal Chemistry

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“…Anomeric mixtures of allyl 2,3:5,6-di-0-isopropylidenemannofuranosides have also been reported 24 using CH 2 =CHCH 2 OH and P(NMe 2 ) 3 in CC1 4 . The O-allyl sugar ethers were generally made via modified standard methods by allylation of free hydroxy groups in the carbohydrate precursors.…”

Section: Resultsmentioning

confidence: 89%

O-(3-STANNYLPROPYLOXY) CARBOHYDRATE DERIVATIVES via HYDROSTANNYLATION OF O-ALLYL CARBOHYDRATE COMPOUNDS

Garden¹,

Wardell²

1997

Main Group Metal Chemistry

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Various 0-(3-triorganostannyl)propyl carbohydrate derivatives have been synthesised by hydrostannylation of selected O-allyl mannose, glucose and lactose derivatives, containing both protected and free hydroxyl groups, and possessing either furanose and pyranose rings: both mono-and disaccharide derivatives have been obtained. Characterisation of the products has been 113 119carried out using H, C and Sn NMR spectroscopy. The conformations of the carbohydrate rings are not affected by the large, but remote, organotin substituents. 13 sugar (e.g. 8 and 9) linkages. Compound 7 was obtained by Bu 3 SnH addition to an acetylenic sugar, while 8 and 9 were produced by Ph 3 SnH addition to appropriate galactosyl allyl ethers. Compounds, 8 and 9, until the present communication, were the only known examples of compounds having Sn-(CH 2 )30-sugar linkages. Among the 0-3-(triorganostannyl)propyl saccharides (1-6), now reported, are compounds having free hydroxyl groups as well as those possessing ester and isopropylidene protected hydroxyl groups. As well as details of the synthesis and spectral properties of 1-6, some preliminary results of the chelating abilities of the saccharide groups in 0-3-(iodo-organostannyl)propyl saccharide derivatives, (1-6: R or are also reported. 711Brought to you by | Purdue University Libraries EXPERIMENTAL NMR spectra were obtained on a Bruker 250 MHz instrument and IR spectra on Philips Analytical PU 9800 FTIR and Nicolet 205 FTIR instruments. Triphenvltin hydride, 15 dimethylphenyltin hydride, 15 tetra-O-acetyl-a-D-glucopyranosyl bromide, 1 2,3:5,6-di-0-17 · 17 isopropylidene-D-mannofuranose, l,2:5,6-di-0-isopropylidene-a-D-glucofuranose and hepta-O-acetyl-lactosyl bromide 18 were prepared by published procedures. Solvents were purified and dried by standard means.Brought to you by | Purdue University Libraries Allyl 2,3:5,6-di-0-isopropylidene-a-and -ß-D-mannofuranose (10 and 11, respectively). An excess ofNaH (0.4 g) was added to a mixture of 2,3:5,6-di-O-isopropylidene-a-andß-D-mannofuranose (2.22 g, 8.5 mmol) in dry ether (20 ml). Excess allyl bromide (5.16 g, 43 mmol) and a catalytic amount of NBu 4 Br (ca. 5 mg) were added and the reaction mixture refluxed for 10h (TLC, irrigant,:ethyl acetate, 2:3 v/v indicated complete reaction). Water (20 ml) was added to the reaction mixture. The ethereal solution was collected, dried over calcium chloride and rotary evaporated to give, as indicated by 'h NMR spectroscopy, a colourless 1:3.7 mixture of the α and β anomers of allyl 2,3:5,6-di-0-isopropylidene-Dmannofuranose: these were separated by column chromatography using ethyl acetate:pet.ether (60-80°C) (3:2 v:v) as the eluent. Yields of the α and β anomers, isolated as oils, were 17 and 60% respectively. A similar reaction carried out in DMF produced a 1:1 mixture of anomers. 'h and ,3 C NMR spectra data of the separated anomers are given in Tables 1 and 2. Allyl ot-D-mannopyranoside (12).A mixture of D-mannose (1.00 g, 5.55 mmol), allyl alcohol (12 ml) and Zeo-karb 225 acid resin (0.5 g) ...

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“…27 The Sn(IV) complexes of the general formula 15 are the most extensively documented in the literature. 28 ± 30 Organotin compounds with organometal fragments directly bound to the carbohydrate core 31,32 are characterised by intramolecular coordination of the type 16a. 31 The stannylene carbohydrate acetals 17 form dimers 18.…”

Section: Complexes With P-metal Cationsmentioning

confidence: 99%

“…28 ± 30 Organotin compounds with organometal fragments directly bound to the carbohydrate core 31,32 are characterised by intramolecular coordination of the type 16a. 31 The stannylene carbohydrate acetals 17 form dimers 18. 33,34 Some analogous derivatives form trimers and even pentamers.…”

Section: Complexes With P-metal Cationsmentioning

confidence: 99%