183871-36-5

Usage

Uses

Used in Pharmaceutical Research:
[(2S,3S)-2-(benzyloxy)pentan-3-yl]hydrazine is used as a building block for the synthesis of various pharmaceutical intermediates, due to its unique structural features that can be further modified to create bioactive compounds.
Used in Organic Synthesis:
In the field of organic synthesis, [(2S,3S)-2-(benzyloxy)pentan-3-yl]hydrazine is used as an intermediate in the synthesis of complex organic molecules, leveraging its reactive functional groups for the formation of new chemical entities.
Used in the Synthesis of Bioactive Compounds:
[(2S,3S)-2-(benzyloxy)pentan-3-yl]hydrazine is employed as an intermediate for the synthesis of bioactive compounds, where its hydrazine and benzyloxy functionalities can be exploited to develop molecules with potential therapeutic properties.
Safety Considerations:
It is important to handle [(2S,3S)-2-(benzyloxy)pentan-3-yl]hydrazine with care, as it can be harmful if swallowed, inhaled, or comes into contact with skin. Proper safety measures should be taken during its use to minimize health risks.

Upstream product

• 17026-42-5 O,O'-dibenzoyl-D-tartaric acid 
• 122151-32-0 (S)-2-(benzyloxy)-1-(pyrrolidin-1-yl)propan-1-one 
• 132489-33-9 (S)-2-benzyloxy-3-pentanone 

Downstream Products

• 1621922-54-0 ethyl 3-(4-(1-((2S,3S)-2-hydroxypentan-3-yl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)phenyl)propanoate 
• 1621922-42-6 3-(4-(1-((2S,3S)-2-hydroxypentan-3-yl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)phenyl)propanoic acid 
• 1621922-52-8 ethyl 3-(4-(1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)phenyl)propanoate 

Relevant academic research and scientific papers

Preparation method of posaconazole intermediate

The invention discloses a preparation method of a key intermediate POB for preparing posaconazole. Firstly, BP004b04 and oxalic acid are salified to obtain POE; secondly, the POE reacts with di-tert-butyl dicarbonate in the presence of a base to obtain POP, and the POP is recrystallized; thirdly, the POP and POK react with each other in the presence of a base to obtain POR, and POS is obtained after a tert-butyl carbonate protecting group of the POR is removed; finally, the POS is subjected to ring closure to obtain the POB. By means of the method, in the obtained POB, the content of diastereomers is smaller than or equal to 0.01%, and the total yield of the entire route is high.

Preparation method of high-purity posaconazole

The invention discloses a preparation method of posaconazole, comprising: subjecting BP004b04 and oxalic acid to salt forming to obtain POE; subjecting POE and di-tert-butyl decarbonate to reaction inthe presence of a base to obtain POP, and recrystallizing POP; subjecting POP and POK o reaction in the presence of a base to obtain POR, and removing tert-butyl carbonate protecting group from POR to obtain POS; subjecting the POS to ring closing to obtain POB; subjecting the POB and POA to reaction to obtain posaconazole. Posaconazole prepared via the preparation method has the content of diastereoisomers being /=0.01%, and the overall route has high total yield.

Intermediate for preparing posaconazole

The invention discloses an intermediate POP for preparing posaconazole. A structure of the intermediate is as shown in the specification. By using the intermediate to prepare POB, the obtained POB hasa diastereomer content being smaller than or equal to 0.01%, and the total yield of the overall route is relatively high.

A PROCESS FOR THE MANUFACTURE OF POSACONAZOLE

The present invention discloses an improved process for the manufacture of Posaconazole, an anti-fungal agent belonging to the category of substituted Tetrahydrofuran Triazole compound. The present invention further describes preparation of formula A and formula B, the key intermediates in the preparation of Posaconazole. The invention also discloses novel intermediates that are useful in the synthesis of Posaconazole.

Method for preparing chiral hydrazine

The invention discloses a method for preparing chiral hydrazine. The method comprises the following steps: (2S)-2-benzyloxy-1-(1-pyrrolidyl)-1-acetone is used as a starting material, a Grignard reaction is performed, carbonyl is reduced after ethyl is introduced, and hydroxyl is obtained; crystalizaiton for purification is performed after a reaction with a sulfonylation reagent, then a reaction with hydrazine hydrate is performed, salt formation is performed by adopting dibenzoyl-L-tartaric acid monohydrate, and a compound IV is obtained after free hydrazine is acylated, and is an important intermediate for preparing posaconazole. The method has the advantages that the operation is easy to perform, pollution to the environment is low, the product optical selectivity is high, the proportion of a (3S) isomer to a (3R) isomer reaches 94.6: 5.4 after the purification operation on a compound X, and the method is suitable for being applied to industrial production of posaconazole.