Synthetic method for sulforaphane

A technology of sulforaphane and methylthiobutyl, which is applied in the field of synthesis of natural product sulforaphane, can solve the problems of cumbersomeness, high cost, high toxicity, etc., and achieve the effect of avoiding hydrazinolysis reaction and easy operation
CN102249968BActive Publication Date: 2013-07-17江苏宁录科技股份有限公司
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
江苏宁录科技股份有限公司
Publication Date
2013-07-17

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Abstract

The synthesis method of sulforaphane of the present invention belongs to the field of medicine synthesis. After the amino group in 4-amino-1-butanol is protected by the Boc group, its hydroxyl group is converted into a methylsulfonyl ester by methylsulfonyl chloride, and then reacted with sodium methylthiolate to generate 4-methylthiobutyl-1 - tert-butoxyamide. Under acidic conditions, the Boc protecting group is removed to obtain 4-methylthio-1-butylamine. The latter reacted with carbon disulfide for 1 hour in the presence of triethylamine, and then added p-toluenesulfonyl chloride for half an hour to generate 4-methylthiobutyl-1-thioisocyanate. Finally m-CPBA is oxidized to produce sulforaphane. The present invention avoids the complex phthalimide hydrazinolysis reaction in post-treatment, and does not need to use toxic thiophosgene to prepare thioisocyanate; the total yield is 64%, significantly higher than the total yield of 8% reported in the literature The whole preparation process is easy to operate, saves time, and is suitable for large-scale production.
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Description

technical field

[0001] The invention relates to a new method for synthesizing natural product sulforaphane, which has cancer prevention and other important biological activities, and belongs to the field of drug synthesis. Background technique

[0002] Sulforaphane, also known as sulforaphane, English name is Sulforaphane, CAS number 4478-93-7, molecular formula C 6 h 11 NOS 2 , molecular weight 177.30. Sulforaphane is a thioisocyanate compound, first discovered in 1992 by researchers from Johns Hopkins University in the United States from broccoli sprouts (Proceedings of the National Academy of Sciences, USA. 1992, 89: 2399-2403 ). This compound is also found in other cruciferous vegetables such as kale, bok choy, cauliflower, kohlrabi, mustard greens, radishes, and watercress, usually in the form of glucosinolates. When the plant is broken (such as chewed), glucosinolates are converted into the active ingredient sulforaphane. The sprouts of broccoli and cauliflower...

Claims

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