PRODUCTION OF NATURAL SPHINGOSINES AND SYNTHETIC INTERMEDIATE THEREOF

Title:

PRODUCTION OF NATURAL SPHINGOSINES AND SYNTHETIC INTERMEDIATE THEREOF

Document Type and Number:

Japanese Patent JP2560250

Kind Code:

B2

Abstract:

PURPOSE: To obtain the compound from inexpensively and readily obtainable starting raw materials by reacting N-benzoyl-D-glucosamine with an acetalizing agent, then reducing, sulfonylating, deacetalizing, iodizing and treating with a base.
CONSTITUTION: N-Benzoyl-D-glucosamine is reacted with an acetalizing agent to give a 4,6-acetal of the formula I (Bz is benzoyl R4 is a 1-4C alkyl or phenyl; R6 is H, a 1-4C alkyl, etc.). The compound is reduced to obtain a 2-benzamido-2- deoxy-D-glucitol derivative. The derivative is simultaneously sulfonylated and made into an oxanoline derivative to obtain a phenyloxazoline derivative of the formula II (Ph is phenyl; R is a 1-4C acetal or an aryl), which is acetalized, the iodized and simultaneously eliminated reductively to give an end vinyl compound of the formula III. The compound is treated with a base, the prepared epoxide is reacted with a dodecyl Grignard reagent in the presence of a curpous salt, the oxanoline ring is cleft and the benzonyl group is eliminated to obtain the compound of the formula IV (R1 to R3 each is H).

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Inventors:

MURAKAMI TEIICHI
NAMIKAWA HIROYUKI
HADO MASAKATSU

Application Number:

JP7408594A

Publication Date:

December 04, 1996

Filing Date:

March 18, 1994

Export Citation:

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Assignee:

KOGYO GIJUTSUIN

International Classes:

C07D319/06; B01J27/135; C07B61/00; C07C213/02; C07C215/24; C07D263/14; C07D319/20; C07D413/06; (IPC1-7): C07C215/24; C07C213/02; C07D263/14; C07D319/06; C07D319/20; C07D413/06

Other References:

ＬＩＥＢＩＧＳＡＮＮ．ＣＨＥＭ．，１９９０，（１１），１０６９−１０７８
ＬＩＥＢＩＧＳＡＮＮ．ＣＨＥＭ．，１９９１，（４），３４９−３５６
天然有機化合物討論会講演要旨集，１９８９，３１ＳＴ，Ｐ．２２−２９

Attorney, Agent or Firm:

Director, Institute of Materials Technology, Institute of Industrial Technology

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