(2S,3R,4R,5R)-3,4-Dihydr­oxy-5-(hydroxy­meth­yl)pyrrolidine-2-carboxylic acid [(2S,3R,4R,5R)-3,4-dihydr­oxy-5-(hydroxy­meth­yl)proline]

نویسندگان

  • Daniel Best
  • Sarah F. Jenkinson
  • Amber L. Thompson
  • David J. Watkin
  • Francis X. Wilson
  • Robert J. Nash
  • George W. J. Fleet
چکیده

The crystal structure of the title compound, C(6)H(11)NO(5), establishes the relative configuration at the four stereogenic centres; the absolute configuration is determined by the use of d-glucuronolactone as the starting material for the synthesis. Mol-ecules are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds into a three-dimensional network, with each mol-ecule acting as a donor and acceptor for five hydrogen bonds.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

5-{(2S,3R,4S,5S,6R)-3,4-Dihydr­oxy-6-hydroxy­meth­yl-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydr­oxy-6-methyl­tetra­hydro­pyran-2-yloxy]tetra­hydro­pyran-2-yloxy}­-7-hydr­oxy-2-(4-hydroxy­phen­yl)chromen-4-one monohydrate

In the title compound, C(27)H(30)O(14)·H(2)O, the hydroxy-phenyl ring makes a dihedral angle of 20.05 (11)° with the chromenone ring system. The crystal structure is stabilized by intra- and inter-molecular O-H⋯O hydrogen bonds. The absolute configuration was assigned on the basis of an analagous structure.

متن کامل

Studies on the constituents of Broussonetia species X. Six new alkaloids from Broussonetia kazinoki Sieb.

Six new alkaloids, broussonetines W, X, M1, U1, J3, and J2 (1-6) were isolated from the branches of Broussonetia kazinoki SIEB. (Moraceae) as minor constituents. They were formulated as (2R,3R,4R,5R)-2-hydroxy-methyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyllpyrrolidine (1), (2R,3S,4R,5R)-2-hydroxymethyl-3,4-dihydroxy-5-17-(cyclohexy-2-on-1(6)-enyl)heptyl]pyrrolidine-4-O-beta-D-glucop...

متن کامل

[Stereoselective synthesis of polyhydroxylated amines using (S)-pyroglutamic acid derivatives].

Naturally occurring polyhydroxylated amines such as (+)-1-deoxynojirimycin, polyoxamic acid, anisomycin, (-)swainsonine, and alexine stereoisomers, which have interesting biological activities including glucosidase- and mannosidase-inhibitory activity, immunoregulatory activity, and antibacterial effects, were synthesized stereoselectively starting from (S)-pyroglutamic acid derivatives. α,β-Un...

متن کامل

Analogues of Methyl Y)-Ribo- and D-Arafo/io-furanosides Having Phosphorus in the Anomeric Position+

Recently, we have completed syntheses of (2R , 3R , 4R)-3-C-(hydroxym ethyl)-2-m ethoxy-2-oxo-l,2oxaphospholane-3,4-diol as well as of (2R , 3R , 4S, 5R )and (2S, 3R , 4S, SR ^^'-O -benzylid en e-S-O (terr-butyldimethylsilyl)-5-C-(hydroxymethyl)-2m ethoxy-2-oxo-l,2-oxaphospholane-3,4-diol which were considered as analogues of C-2 branched-chainD-threose and D-lyxose containing phosphorus in the...

متن کامل

Stereoselective Synthesis of Unnatural Analogs of (1)- Casuarine from Partially Protected DGDP

A new synthetic approach to analogs of (þ)-casuarine (2a and 2b), a natural pentahydroxylated pyrrolizidinic alkaloid in a highly stereocontrolled manner, is reported herein. An orthogonally protected polyhydroxylated pyrrolidine, such as (2S,3R,4R,5R)-3,4-dibenzyloxy-20-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine [3, protected DGDP (2,5-dideoxy-2,5-imino-D-glucitol)], easily av...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 65  شماره 

صفحات  -

تاریخ انتشار 2009