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Preparation and properties of triorganostannylmethyl 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosides; pesticidal and fungicidal activities of triphenylstannyl-carbohydrate derivates

✍ Scribed by Christine R McDonough; Oonah J Taylor; James L Wardell

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
534 KB
Volume
3
Category
Article
ISSN
0268-2605

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✦ Synopsis

The synthesis of trioganostannylmethyI2,3:5,6-di-0-isopropylidene-wD-mannofuranoside (compound 3, R*OCHzSnRzR':R=R'=Me or Ph) from D-

is transmetallated by PhLi to compound 5 , R*OCHzLi, which can be trapped by HgClZ [as (R*OCHz)zHg] and by ketones, R3COMe [as compound 7, R*OCH2CR3MeOH]. Two stereoisomers of this compound (7a, R3=Ph) were formed in a ratio of 40:60, indicating some asymmetric induction, arising from the chiral R* moiety. Reactions of compound 3, (R=R'=Ph), with Iz, HOZCCF3 and CIzPtCOD result in Ph-Sn bond cleavage and formation of compound 3 with R = Ph; R'=I, OCOCF3 and CI respectively. Reactions of compound 3 (R = R ' =Me) with electrophiles can lead to cleavage of either or both types of C-Sn bonds present (e.g. by 12, Brz, C1,PtCOD or SnClJ or to attack at the C5-Cs protecting group with release of acetone (e.g. by CF3COZH, SOz or CH3COCl). Pesticidal and fungicidal activities of compound 3(R=R' =Ph) as well as of 1,2:5,6-di-O-isopropylidene-3-O-(triphenylstannylmethyl)-a!-D-glucofuranose (compound 2, R = Ph) and methyl 4, 6-O-benzylidene-2-deoxy-2-triphenylstannyl-a!-Daltropyranoside (compound 1, R= Ph) are reported.

📜 SIMILAR VOLUMES

X-ray and conformational investigation o
X-ray and conformational investigation of 6-deoxy-6-C-(1,5-di-O-acetyl-2,3-O-isopropylidene-β-d-allo-pentofuranos-5-yl)-1,2:3,4-di-O-isopropylidene- α-d-galactopyranose and 6-C-(benzyl 5-deoxy-2,3-O-isopropylidene-β-d-ribofuranosid-5-yl)-1,2:3,4-di-O-isopropylidene- d-glycero-α-d-galacto-hexopyranose
✍ Janusz W. Krajewski; Wojciech Karpiesiuk; Anna Banaszek 📂 Article 📅 1994 🏛 Elsevier Science 🌐 English ⚖ 523 KB

The structures of the title compounds (2b and 3) have been investigated in the solid state by X-ray methods. The crystals of 2b are monoclinic, space group P2,, and of 3 orthorhombit, space grtup P2,2,2,. The cell dimensions are: for 2b, a = 9.910(2), b = 11;745W, c = 11.810(3) A, /3 = 97.32(l)"; a

ChemInform Abstract: Septanose Carbohydr
ChemInform Abstract: Septanose Carbohydrates. Part 6. Preparation of 1,2-O-Isopropylidene Derivatives of α-D-Galactoseptanose, β-L-Altroseptanose, and 3-O-Methyl-α-D-guloseptanose.
✍ Graham E. Driver; John D. Stevens 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB 👁 2 views

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