133329-79-0

Upstream product

• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 

Downstream Products

• 133329-85-8 (1R,2S,4R)-2-Methoxy-4-methyl-1-(4-methyl-furan-2-yl)-5-trityloxy-pentan-1-ol 
• 133329-85-8 (1S,2S,4R)-2-Methoxy-4-methyl-1-(4-methyl-furan-2-yl)-5-trityloxy-pentan-1-ol 
• 133329-90-5 (2S,3S,5S,6R)-2,5-Dimethoxy-6-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-3-methyl-tetrahydro-pyran 
• 133329-90-5 (2S,3R,5S,6R)-2,5-Dimethoxy-6-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-3-methyl-tetrahydro-pyran 
• 133329-87-0 (2R,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one 
• 133329-89-2 (2R,3S,6S)-3,6-Dimethoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran 
• 133329-88-1 (2S,3S,6S)-6-Methoxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-3,6-dihydro-2H-pyran-3-ol 
• 133329-86-9 (2R,6S)-6-Hydroxy-2-((1S,3R)-1-methoxy-3-methyl-4-trityloxy-butyl)-5-methyl-6H-pyran-3-one 
• 133329-84-7 (2S,4R)-2-Methoxy-4-methyl-5-trityloxy-pentanal 
• 133329-83-6 (2S,4R)-2-Methoxy-4-methyl-5-trityloxy-pentan-1-ol 
• 136262-60-7 (2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2-methoxy-4-methylpentanal 

Relevant academic research and scientific papers

Multi-Gram Scale Synthesis of Chiral 3-Methyl-2,5-trans-tetrahydrofurans

In this article, we report the rapid and facile synthesis of chiral 3-methyl-2,5-trans-tetrahydrofurans. This reaction utilizes cheap and easily available starting materials. A domino hydrolysis and intramolecular Michael-type ring closure reaction was the key step. As a result, synthesis of the desired 3-methyl-2,5-trans-tetrahydrofurans could be achieved in gram-scale over seven linear steps with high chemical yield and high diastereoselectivity.

A transition metal-catalyzed enyne metathesis for the preparation of pyrrolizidine alkaloid core: Application towards the total synthesis of stemaphylline

In this paper, we disclose an efficient route for the synthesis of pyrrolizidine alkaloid core and its application towards the total synthesis of stemaphylline. The key pyrrolizidine core was achieved with Ru-carbene catalyzed ring closing enyne metathesis (RCEM). The effect of different types and amounts of Ru-carbene catalysts, solvents and temperature were systematically studied. The advantage of this method includes the construction of pyrrolizidine alkaloid core in a single operation.

Method for highly selective synthesis of multi-chiral central tetrahydrofuran ring

The invention relates to the technical field of organic synthesis, in particular to a method for highly selective synthesis of a multi-chiral central tetrahydrofuran ring. The method has mild conditions, simple reaction steps, easy operation, high regioselectivity and high stereoselectivity. The method comprises the following steps: (a) using L-glutamic acid 1 as a starting material, and carryingout diazotization and ring-closing to obtain a lactone intermediate 2; (b) reducing the carboxyl group in the lactone intermediate 2 to obtain an intermediate 3; (c) protecting the hydroxyl group in the intermediate 3 by TBS to obtain an intermediate 4; (d) carrying out a substitution reaction of the intermediate 4 to obtain an intermediate 5; (e) reducing the intermediate 5 to obtain a precursorcompound of an intermediate 6; (f) carrying out a Wittig reaction of the precursor compound of the intermediate 6 to obtain the intermediate 6; (g) carrying out a Mitsunobu reaction of the intermediate 6 to obtain an intermediate 7; and (h) performing protective group removal and ring-closing on the intermediate 7 under the action of a base to obtain a target product 8.