124388-95-0Relevant academic research and scientific papers
Total Synthesis of (2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate, a Partially Protected Ceramide Part of Sponge Cerebrosides
Nakashima, Hideki,Hirata, Norihiko,Iwamura, Takeru,Yamagiwa, Yoshiro,Kamikawa, Tadao
, p. 2849 - 2858 (1994)
(2S,3S,4R)-2--16-methylheptadecane-1,3,4-triol 3,4-dibenzoate 32, apertially protected ceramide part of a cerebroside from the marine sponge Halichondria japonica, has been synthesized from L-ascorbic acid, and its absolute stereochemistry has been determined.The key steps in the synthesis include the regioselective ring opening of chiral epoxide 5 with a 2-alkyl-2-lithio-1,3-dithiane and the introduction of a hydroxymethylene synthon using Dondoni's protocol to assemble C(1) and C(2) functionality.
Structural and Functional Analysis of Bacterial Sulfonosphingolipids and Rosette-Inducing Factor 2 (RIF-2) by Mass Spectrometry-Guided Isolation and Total Synthesis
Beemelmanns, Christine,Jautzus, Theresa,King, Nicole,Leichnitz, Daniel,Peng, Chia-Chi,Ragu?, Luka,Regestein, Lars,Rutaganira, Florentine U. N.
supporting information, (2022/01/04)
We have analyzed the abundance of bacterial sulfonosphingolipids, including rosette-inducing factors (RIFs), in seven bacterial prey strains by using high-resolution tandem mass spectrometry (HRMS2) and molecular networking (MN) within the Glob
An asymmetric synthesis of sulfobacin A
Sharma, Anubha,Gamre, Sunita,Chattopadhyay, Subrata
, p. 3705 - 3707 (2008/02/09)
A facile synthesis of sulfobacin A has been developed starting from (R)-cyclohexylideneglyceraldehyde (11). The key steps in the synthesis are the highly diastereocontrolled allylation of 11 and syn-selective reduction of a ketone derived from 11. The oth
CONVENIENT SYNTHESES OF SIX TUNICAMYCIN ACIDS
Grzeszczyk, B.,Konowal, A.,Zamojski, A.
, p. 1627 - 1632 (2007/10/02)
10-Methylundecanol (15), obtained in five steps from sebacic acid, served as substrate for the synthesis of the ester 3-Et, via oxidation to aldehyde and Wittig condensation with stabilized ylid.From 3-Et next ester, 2-Et, was obtained by hydrogenation.Reduction of the ester grouping in 2-Et to the alcohol, followed by oxidation to aldehyde provided a substrate for another Wittig condensation leading to 8-Me.On the other hand, bromide 17, obtained from 15, was used for alkylation of propargylic alcohol.The product obtained, 18, served for the synthesis of acids 5 and 6.Ester 10-Et was obtained from 18 via hydrogenation of the triple bond, oxidation to aldehyde and condensation with a stabilized Wittig ylid.The yields of all steps were good to excellent. Key words: higher fatty acids, tunicamycin acids.
Synthesis of 14-methylpentadecan-3-one and 2-methylheptadecane
Kad, G. L.,Gupta, Sangita
, p. 581 - 583 (2007/10/02)
Li2CuCl4 catalysed coupling of 1-tetrahydropyranyloxy-8-octanylmagnesium bromide (III) with isobutyl bromide yields IV which on depyranylation with PPTS/MeOH followed by treatment with PBr3 affords the key intermediate 1-bromo-10-methylundecane (VI).Regioselective alkylation of α-lithio-2-butanone N,N-dimethylhydrazone with VI in THF at -78 deg C followed by oxidative hydrolysis with aq.NaIO4 at pH 7 results in the formation of 14-methylpentadecan-3-one (I).Coupling of VI with hexylmagnesium bromide using Li2CuCl4 as catalyst furnishes the target compound (II).
