Iodocyclofunctionalization of (Z)-1-Trichloroacetimidoyloxyalk-2-enes and 3-Trichloroacetimidoyloxyalk-1-enes. Synthesis of (+/-)-erythro-Sphinganine Triacetate and (+/-)-threo-Sphinganine Triacetate

DOI: 10.1039/P19860001339

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 1339 - 1344 (1986)

Update date:2022-08-05

Topics:

Authors:

Bongini, Alessandro

Cardillo, Giuliana

Orena, Mario

Sandri, Sergio

Tomasini, Claudia

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P19860001339

(Z)-1-Trichloroacetimidoyloxyoctadec-2-ene, easily obtained from (Z)-octadec-2-en-1-ol, was iodocyclized with N-iodosuccinimide to give the 4-(1-iodohexadecyl)-2-trichloromethyl-4,5-dihidro-oxazole.From this compound, two routes were developed, either to pure (+/-)-erythro-sphinganine triacetate or to pure (+/-)-threo-sphinganine triacetate, respectively.The neutral cleavage of 4-(1-iodohexadecyl)-2-trichloromethyl-4,5,-dihydro-oxazole gave the corresponding amide which, by treatment with Amberlyst A 26 (CO3(2-) form), afforded the cis-4-hydroxymethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazole together with a minor amount of cis-2-hydroxymethyl-3-pentadecylaziridine.After hydrolysis of the oxazole and full acetylation, (+/-)-erythro-sphinganine triacetate was obtained in 70 percent yield.On the other hand, acidic cleavage of the 4-(1-iodohexadecyl)oxazole 2-amino-3-iodo-octadecan-1-ol hydrochloride, which was directly treated with Amberlyst A 26 (AcO(-) form).The product was acetylated and (+/-)-threo-sphinganine triacetate was recovered in 70 percent yield after chromatographic separation.As an alternative, 3-trichloroacetimidoyloxyoctadec-1-ene was cyclized with N-iodosuccinimide to give a 20:80 cis:trans mixture of 4-iodomethyl-5-pentadecyl-2-trichloromethyl-4,5-dihydro-oxazoles.After ring cleavage, the corresponding ring-opened hydrochlorides were obtained.The mixture was then treated with Amberlyst A 26 (AcO(-) form) and the product was directly acetylated.After silica gel chromatography, (+/-)-threo-sphinganine triacetate and (+/-)-erithro-sphinganine triacete were obtained in good yield, in the ratio 80:20.

Full text of DOI:10.1039/P19860001339

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:(2S,3R)-2-Amino-octadecane-1,3-diol; hydrochloride

Cas No:111168-12-8

R&D Labs maybe for 111168-12-8

Suzhou Wedo Chemicals Co., Ltd.

Contact:86 512 58100425

Address:Zonger Road, DongSha Industry Park , Zhangjiagang, Jiangsu, China
Esuccess Material Limited

Contact:852-29282288

Address:HONGKONG
SINO GREAT ENTERPRISE LTD.

Contact:+86-731-84427351

Address:154 JIANXIANG SOUTH ROAD
NINGBO YINLIANG FOREIGN TRADE CO., LTD.

Contact:+86-574-87834016 / 87898057

Address:23F NO.666JINYU ROAD,YINGZHOU DISTRICT,NINGBO.CHINA
Jinzhou Jiutai Pharmaceutical Co.,Ltd

Contact:+86-0416-5179890

Address:No.41, Taianli, Taihe District, Jinzhou, Liaoning

Relevant to this article

Doi:10.1021/op200186d
(2011)
New pyridine ONN-pincer gold and palladium complexes: Synthesis, characterization and catalysis in hydrogenation, hydrosilylation and C-C cross-coupling reactions

Doi:10.1002/adsc.200700209
(2007)
AROMATIC DERIVATIVES OF 2,3-DIHYDRO-1H-1,5-BENZODIAZEPINE

Doi:10.1007/BF00761991
(1987)
6-(2-Adamantan-2-ylidene-hydroxybenzoxazole)-O-sulfamate: A potent non-steroidal irreversible inhibitor of human steroid sulfatase

Doi:10.1016/j.bmcl.2003.09.050
(2003)
Synthesis and evaluation of [O-methyl-¹¹C]4-[3-[4-(2- methoxyphenyl)- piperazin-1-yl]propoxy]-4-aza-tricyclo[5.2.1.02,6]dec-8-ene-3,5- dione as a 5-HT_1A receptor agonist PET ligand

Doi:10.1002/jlcr.1475
(2008)
Synthesis, structures, and reactions of dirhodium complexes bearing a 1,2-Diphenyl-3,4-diphosphinidenecyclobutene ligand (DPCB)

Doi:10.1021/om8010799
(2009)

Article Doi