PRODUCTION OF DERIVATIVE OF 6-DEOXY-6,6,6-TRIFLUOROSACCHARIDES

Title:

PRODUCTION OF DERIVATIVE OF 6-DEOXY-6,6,6-TRIFLUOROSACCHARIDES

Document Type and Number:

Japanese Patent JP3662954

Kind Code:

B2

Abstract:

PURPOSE: To obtain the subject compound, useful for a raw material, etc., for liquid crystals, medicines, agrochemicals, etc., by optically resolving a recemic 1-benzyloxy-6,6,6-trifluoro-4-hexyn-3-ol, then carrying out the reduction of the (S)-isomer into an olefin and conversion into a diol, etc.
CONSTITUTION: This method for producing a derivative of 6-deoxy-6,6,6- trifluorosaccharides represented by formula V (R1 and R2 are each an alkyl or an aryl) comprises optically resolving a recemic 1-benzyloxy-6,6,6-trifluoro-4- hexyn-3-ol represented by formula I, then reducing the resultant (S)-isomer in the presence of sodium hydride-bis(methoxyethoxy) aluminum, stereospecifically reduce the triple bond, providing (S, E)-1-benzyloxy-6,6,6- trifluoro-4-hexen-3-ol represented by formula II, subsequently oxidizing the resultant compound in the presence of osmimium tetroxide, afford a triol derivative represented by formula III, then converting the resultant triol derivative into an acetonide, debenzylating the prepared compound represented by formula IV and subsequently oxidizing the debenzylated compound. The resultant derivative is useful for liquid crystal materials, an intermediate for medicines, agrochemicals, etc.

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Inventors:

Tomoya Kitazume
Takashi Yamazaki
Akio Watanabe

Application Number:

JP21371794A

Publication Date:

June 22, 2005

Filing Date:

September 07, 1994

Export Citation:

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Assignee:

Toso-F-Tech Co., Ltd.

International Classes:

C07H9/04; C07H23/00; (IPC1-7): C07H9/04; C07H23/00

Other References:

Takashi Yamazaki, Kenji Mizutani, and Tomoya Kitazume,Journal of Organic Chemistry,1995年,Vol.60, No.19,p.6046-6056
Kenji Mizutani, Takashi Yamazaki, and Tomoya Kitazume,Journal of the Chemical Society, Chemical Communications,1995年,No.1,p.51-2

Attorney, Agent or Firm:

Masayuki Kishida
Koji Shinbe
Kotaro Tani

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