74518-57-3 Usage
Occurrence
A glucosidic sulphur-containing alkaloid, xylostosidine occurs in the water-soluble fraction
of the extract of Lonicera xylosteum. It forms colourless needles when crystallized from
MeOH and is laevorotatory with a specific rotation of [α]D -289.37° (c 0.56, MeOH).
The ultraviolet spectrum in MeOH consists of a single absorption maximum at 238 nm.
Acetylation furnishes the tetraacetate which is laevorotatory with a specific rotation of
[α]D20D -85.35° (c 0.35, CHCl3).
Check Digit Verification of cas no
The CAS Registry Mumber 74518-57-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,4,5,1 and 8 respectively; the second part has 2 digits, 5 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 74518-57:
(7*7)+(6*4)+(5*5)+(4*1)+(3*8)+(2*5)+(1*7)=143
143 % 10 = 3
So 74518-57-3 is a valid CAS Registry Number.
InChI:InChI=1/C18H25NO8S/c1-2-8-9-5-12-19(3-4-28-12)16(24)10(9)7-25-17(8)27-18-15(23)14(22)13(21)11(6-20)26-18/h2,7-9,11-15,17-18,20-23H,1,3-6H2/t8-,9+,11?,12+,13?,14?,15?,17+,18?/m1/s1
74518-57-3Relevant articles and documents
Iridoids, 24. - Biomimetic Synthesis of the Monoterpene Alkaloids Xylostosidine and Loxylostosidine A and of Similar Unnatural Compounds by Transformations of the Monoterpene Glycoside Secologanin
Tietze, Lutz F.,Baertels, Christoph,Fennen, Jens
, p. 1241 - 1246 (2007/10/02)
Condensation of secologanin (1) with cysteamine (5a) affords diastereoselectively 71percent of xylostosidine (2), which was transformed into loxylostosidine A (3) by treatement with m-chloroperbenzoic acid in 70percent yield.Similarly, reaction of the functionalized amines 5b, c, 6a-c, and 7 with 1 yields the unnatural monoterpene alkaloids 8-13.The condensation of 1 with 5a was followed by time-resolved NMR spectroscopy to reveal the stereoselectivity in this transformation.