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Chiral (2,2-dimethyl-1,3-dioxolane-4-yl)hydroxy mesylates, and preparing method and applications thereof

A technology of hydroxymethanesulfonate and dioxolane, which is applied in the field of chiral hydroxymethanesulfonate and its preparation, can solve the problems of not being able to store for a long time, solve the difficulties of transportation and storage, and facilitate long-term storage and transshipment , the effect of structural stability

Active Publication Date: 2015-07-22
宜宾市南溪区红光制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The first object of the present invention is to provide a chiral (2,2-dimethyl-1,3-dioxolan-4-yl) hydroxymethanesulfonate, said chiral (2,2- Dimethyl-1,3-dioxolane-4-yl) hydroxymethanesulfonate has a stable structure, is easy to store and transport for a long time, and the salt also has the same reactivity as chiral mannaldehyde acetone, and can Substitute chiral mannaldehyde acetone for Wittig reaction, overcome the defects that chiral glyceraldehyde acetone is prone to self-polymerization reaction and cannot be stored for a long time, and cannot participate in Wittig reaction after self-polymerization

Method used

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  • Chiral (2,2-dimethyl-1,3-dioxolane-4-yl)hydroxy mesylates, and preparing method and applications thereof
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  • Chiral (2,2-dimethyl-1,3-dioxolane-4-yl)hydroxy mesylates, and preparing method and applications thereof

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preparation example Construction

[0051] Please refer to figure 1 , the preparation method of the above-mentioned chiral (2,2-dimethyl-1,3-dioxolan-4-yl) hydroxymethanesulfonate that the present invention also provides comprises the following steps:

[0052] Step 101: synthesizing chiral glyceraldehyde acetonide;

[0053] Preferably, due to the unstable structure of chiral glyceraldehyde acetone, in order to improve its yield, preferably, this step can be specifically carried out according to the following operations:

[0054] S1: Mix 1,2,5,6-dipropylidene-D-mannitol and dichloromethane, stir and dissolve at 15-25°C, then add saturated bicarbonate and sodium periodate in sequence, and continue to stir for reaction 1 After -4 hours, add anhydrous sodium sulfate / anhydrous magnesium sulfate to dry to obtain a primary mixture;

[0055] In step S1, the amount of each reactant is preferably defined as follows: the molar ratio of 1,2,5,6-dipropylidene-D-mannitol to dichloromethane is 1:(35-60); The molar ratio of ...

Embodiment 1

[0073] The preparation method of the chiral (2,2-dimethyl-1,3-dioxolan-4-yl) hydroxymethanesulfonate provided in the examples of the present invention comprises:

[0074] S11: Oxidation reaction

[0075] Add 1,2,5,6-dipropylidene-D-mannitol (1mol) and dichloromethane (40mol) into the reactor, stir and dissolve at 20°C, then add saturated sodium bicarbonate (0.1mol), Add sodium periodate (1.45mol) in batches under continuous stirring, and keep the reaction temperature below 35°C during the addition of sodium periodate. After adding sodium periodate, continue to stir and react at 25°C for 2h, then add anhydrous sulfuric acid Sodium (1mol) was dried for 60min., and anhydrous sodium sulfate was added, and the reaction temperature did not exceed 30°C. Filtrate to obtain (R) mannaldehyde acetonide dichloromethane solution, and recover the dichloromethane by rotary evaporation at 35-50° C. to obtain colorless and transparent viscous (R) glyceraldehyde acetone.

[0076] S12: Salt fo...

Embodiment 2

[0080] The preparation method of the chiral (2,2-dimethyl-1,3-dioxolan-4-yl) hydroxymethanesulfonate provided in the examples of the present invention comprises:

[0081] S21: Oxidation reaction

[0082] Add 1,2,5,6-dipropylidene-D-mannitol (1.5mol) and dichloromethane (65mol) into the reactor, stir and dissolve at 20°C, then add saturated potassium bicarbonate (0.16mol) , continue to stir and add sodium periodate (1.45mol) in batches, and keep the reaction temperature below 30°C during the addition of sodium periodate. After adding sodium periodate, continue stirring at 25°C for 1.5h, then add Magnesium sulfate water (1.2mol) was dried for 60 min., and anhydrous magnesium sulfate was added, and the reaction temperature did not exceed 30°C. Filtrate to obtain (R) mannaldehyde acetonide dichloromethane solution, and recover the dichloromethane by rotary evaporation at 40-50° C. to obtain light yellow transparent viscous (R) glyceraldehyde acetonide.

[0083] S22: Salt formati...

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Abstract

The invention provides chiral (2,2-dimethyl-1,3-dioxolane-4-yl)hydroxy mesylates, and a preparing method and applications thereof, and relates to the fields of fine chemicals and medical intermediates. The preparing method includes synthesizing chiral glyceraldehyde acetonide, dissolving the chiral glyceraldehyde acetonide with ethanol, adding water and one of potassium metabisulfite, lithium sulfite, lithium bisulfite, potassium bisulfite, calcium bisulfite or magnesium bisulfite, stirring and reacting at 20-50 DEG C, filtering to obtain a head product, and drying the head product to obtain the chiral (2,2-dimethyl-1,3-dioxolane-4-yl)hydroxy mesylates. The chiral (2,2-dimethyl-1,3-dioxolane-4-yl)hydroxy mesylates can participate Wittig reactions, in place of the chiral glyceraldehyde acetonide.

Description

technical field [0001] The invention relates to the technical field of fine organic chemical industry, in particular to a chiral (2,2-dimethyl-1,3-dioxolan-4-yl) hydroxymethanesulfonate and a preparation method thereof and application. Background technique [0002] In the food, medicine and chemical industries, chiral glyceraldehyde acetone is an important precursor for the synthesis of chiral drugs and optically active natural products, and can be used as a cheap chirality-inducing monomer for the synthesis of chiral molecules . The bioactive substances that can be synthesized include: prostaglandins, brefeldin A, triene A4, landiolol, L-hydroxyphenylpiperazine and propranolol, etc. [0003] The Wittig reaction is an extremely valuable method for the direct synthesis of olefins from aldehydes and ketones, and the synthesized products are mainly various compounds containing olefinic bonds. In the related art, in order to obtain the corresponding alkenes, chiral glyceralde...

Claims

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Application Information

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IPC IPC(8): C07D317/20C07D317/30
CPCC07D317/20C07D317/30
Inventor 刘治国谢可钟柳
Owner 宜宾市南溪区红光制药有限公司
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