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ChemicalBook CAS DataBase List Nandrolone
434-22-0

Nandrolone synthesis

5synthesis methods
Nandrolone, 17β-hydroxyester-4-en-3-one (29.1.7), is made from estradiol (28.1.17). The phenol hydroxyl group undergoes methylation by dimethylsulfate in the presence of sodium hydroxide, forming the corresponding methyl ether (29.3.1), and then the aromatic ring is reduced by lithium in liquid ammonia, which forms an enol ether (29.3.2). Hydrolyzing this compound with a mixture of hydrochloric and acetic acids leads to the formation of a keto group, and simultaneous isomerization of the double bond from C5–C10 to position C4–C5 gives the desired nandrolone (29.3.3) [16–19]. Upon necessity of using it in the form of acid esters, the product is acylated by corresponding acid derivatives.

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Yield:434-22-0 53%

Reaction Conditions:

with zygowilliopsis sp. WY7905 in aq. phosphate buffer at 30; pH=8; for 24 h;Enzymatic reaction;stereoselective reaction;

Steps:

2.9. Transformation of C-18, C-19 and C-21 steroids by the resting cells

General procedure: C-18, C-19 and C-21 steroids (0.75 g/l, 1.5 mg), such as estrone(3), 9-dehydroandrostenedione (7), norandrostenedione (9), estra-4,9-diene-3,17-dione (11), 19-hydroxyandrost-4-ene-3,17-dione(13), etc. separately dissolved in Tween 80 (1% w/v) were addedinto 2 ml of reaction mixtures containing glucose (10 g/l, 10 mg)and resting cells (0.2 g wet weight) resuspended in phosphate buffer(100 mM, pH 8.0). The mixture was shaken at 30 C for 24 h,then worked-up and analyzed as described in Section 2.5.

References:

Liu, Yuanyuan;Wang, Yu;Chen, Xi;Wu, Qiaqing;Wang, Min;Zhu, Dunming;Ma, Yanhe [Steroids,2017,vol. 118,p. 17 - 24]

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