Synthesis method of chiral sec-allyl alcohol with hydroxyl ortho-position replaced with halogen atoms

A technology for the synthesis of secondary allyl alcohol and its synthesis method, which is applied in the field of synthesis of chiral secondary allyl alcohol, can solve the problems of low yield, high difficulty in separation and purification, and low stereoselectivity of E-form, and achieve high optical purity and low cost effect

Inactive Publication Date: 2017-04-26
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to aim at the deficiencies in the prior art, to provide a kind of synthesis method of chiral secondary allyl alcohol replaced by chlorine atom in the ortho position of the hydroxyl group, to solve the problem of low optical purity of existing chiral secondary allyl alcohol, E formula The technical problems of low stereoselectivity, difficult separation and purification and low yield

Method used

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  • Synthesis method of chiral sec-allyl alcohol with hydroxyl ortho-position replaced with halogen atoms
  • Synthesis method of chiral sec-allyl alcohol with hydroxyl ortho-position replaced with halogen atoms
  • Synthesis method of chiral sec-allyl alcohol with hydroxyl ortho-position replaced with halogen atoms

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Embodiment Construction

[0029] The embodiments of the present invention are described in detail below: the present embodiment is implemented under the premise of the technical solution of the present invention, and detailed implementation methods and specific operating procedures are provided, but the protection scope of the present invention is not limited to the following implementation example.

[0030] 1. The synthetic reaction formula of (R)-1-chloro-3-(1-phenyl-5-mercaptotetrazole)-2-propanol:

[0031]

[0032] Steps

[0033] Add 1-phenyl-5-mercaptotetrazolium (50g, 280.6mmol), methanol (350mL), epichlorohydrin (23mL, 294.6mmol) and triethylamine (59mL, 420.8mmol) into a 1000mL round bottom flask , and the reaction was stirred overnight at room temperature. Concentrate the reaction solution, add 150mL ethyl acetate, water, 0.1M hydrochloric acid, saturated NaHCO 3 , washed with saturated brine, separated, and the organic phase was dried over anhydrous magnesium sulfate, filtered, and conc...

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Abstract

The invention discloses a method for synthesizing optically-pure chiral sec-allyl alcohol by means of an improved Julia alkylation reaction, and belongs to the technical field of organic synthesis. The method comprises the specific technological steps that high optically-pure epoxy halopropane is subjected to hydroxyl protection after tetrazole-thione nucleophilic ring opening is performed and oxidized into an improved Julia alkylation reagent to be condensed with aldehyde or ketone, hydroxyl protection is removed, and a series of high optically-pure chiral sec-allyl alcohol containing E-type carbon-carbon double bonds can be obtained.

Description

[0001] Technical field: [0002] The invention belongs to the field of organic synthesis chemistry, in particular to a method for synthesizing chiral secondary allyl alcohol in which the ortho position of a hydroxyl group is replaced by a halogen atom. [0003] Background technique: [0004] Chiral secondary allyl alcohol and its derivative fragments widely exist in many natural products and drug molecules, such as statin drugs for lowering blood lipids, calcipotriol for psoriasis treatment, and calcipotriol for psoriasis. Bimatoprost (Bimatoprost) for glaucoma treatment, new anti-cancer drug Epothilone (Epothilone), etc. In addition, optically active allyl alcohol is also an important class of reaction intermediates, which can undergo many chemical transformations, such as Claisen rearrangement or SN2' substitution reaction. The chirality of the C–O bond in allyl alcohol will induce the chirality of the newly generated C–C bond, thereby achieving the transfer of chirality. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/00C07C33/48
CPCC07B2200/07C07C29/00C07D257/04C07F7/1804C07F7/1892C07C33/483
Inventor 范为正唐春雷冯柏年江珊刘发明苏佳鹏
Owner JIANGNAN UNIV
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