780789-22-2

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 780789-26-6 (1R,2S,3S,4R,5S)-4-(4-Methoxy-benzyloxy)-3-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexan-2-ol 
• 780789-17-5 (1R,2R,5S)-2-Allyloxy-3-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-3-enol 
• 780789-04-0 tert-Butyl-[(1S,4S,5R)-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hex-2-en-2-ylmethoxy]-dimethyl-silane 
• 780789-20-0 (1S,2S,3R,4R,5S)-2-Allyloxy-1-hydroxymethyl-4-(4-methoxy-benzyloxy)-6-oxa-bicyclo[3.1.0]hexan-3-ol 
• 780789-21-1 (1S,2S,3R,4R,5S)-2-Allyloxy-4-(4-methoxy-benzyloxy)-3-methoxymethoxy-1-methoxymethoxymethyl-6-oxa-bicyclo[3.1.0]hexane 
• 780789-16-4 (1R,2R,5S)-2-Allyloxy-3-(tert-butyl-dimethyl-silanyloxymethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enol 

Downstream Products

• 780789-23-3 (1R,2R,3S,4R,5S)-2-Azido-3-(4-methoxy-benzyloxy)-4,5-bis-methoxymethoxy-1-methoxymethoxymethyl-cyclopentanol 

Relevant academic research and scientific papers

Novel protection of 1,2-diol for trans-dihydroxycyclopentene ring construction by the C[sbnd]H insertion of alkylidene carbene: Formal total synthesis of (+)-trehazolin

The chiral vicinal diol was protected as 6-methylene-1,4-dioxepane to construct a cyclopentene ring by the C[sbnd]H insertion of alkylidene carbene. The removal of the protecting group was achieved in a few steps, affording the corresponding diol in a reasonable yield. Using these reactions, the known synthetic intermediate for (+)-trehazolin was synthesized from D-diethyl tartrate. In addition, a short route to the intermediate from a D-mannitol derivative was described.

Stereocontrolled synthesis of the aminocyclitol moiety of (+)-trehazolin via C-H insertion reaction of alkylidenecarbene

The aminocyclitol moiety of (+)-trehazolin, a powerful trehalase inhibitor, was synthesized in a stereocontrolled manner from cis-2-butene-1,4-diol via C-H insertion reaction of the alkylidenecarbene, followed by regioselective opening of the epoxide ring