62501-71-7

Upstream product

• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 120-80-9 benzene-1,2-diol 
• 164515-26-8 (2S)-1-(2'-benzyloxyphenoxy)-3-benzyloxy-2-propanol 
• 14618-80-5 (R)-benzyl glycidol 
• 100-44-7 benzyl chloride 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 164515-27-9 (2S)-1-(2'-benzyloxyphenoxy)-2-tosyloxy-3-benzyloxypropane 

Downstream Products

• 98572-00-0 (S)-2-hydroxymethyl-1,4-benzodioxane 
• 70918-53-5 (+)-(2R)-2,3-dihydro-1,4-benzodioxine-2-carboxylic acid 
• 1219800-50-6 (R)-tert-butyl 4-(2,3-dihydrobenzo[b][1,4]dioxine-2-carbonyl)piperazine-1-carboxylate 
• 860173-98-4 (R)-N-(1,4-benzodioxan-2-carbonyl)piperazine 
• 104874-86-4 (R)-doxazosin 
• 70918-54-6 (S)‐1,4‐benzodioxane‐2‐carboxylic acid 
• 1415584-44-9 (S)-N-Boc-(1,4-benzodioxan-2-carbonyl)piperazine 
• 401941-54-6 (S)-N-(1,4-benzodioxan-2-carbonyl)piperazine 
• 104874-86-4 (S)-doxazosin 
• 81602-24-6 (R)-WB-4101 
• 46049-48-3 (R)-2-((amino)methyl)-1,4-benzodioxane 
• 62501-73-9 (2S)-2-(hydroxymethyl)-1,4-benzodioxan tosylate 
• 62501-72-8 (R)-2-hydroxymethyl-1,4-benzodioxane 

Relevant academic research and scientific papers

Preparation method of 1,4-benzdioxan-2-formic acid

The invention provides a preparation method of 1,4-benzdioxan-2-formic acid. The preparation method comprises the following steps: by taking benzylodiglycidyl ether and o-halogen phenol as raw materials, performing cyclization reaction, debenzylation reaction and oxidization reaction to obtain the 1,4-benzdioxan-2-formic acid. The preparation method provided by the invention is simple in reactionprocess; as the benzylodiglycidyl ether and the o-halogen phenol are used as the raw materials for reaction, no pollutants are produced, and no-irritative and no-allergic objects are produced; compared with other existing lines, the preparation method is environmentally friendly, high in total yield and favorable for mass production; the ee value of the finally prepared 1,4-benzdioxan-2-formic acid is more than or equal to 99 percent, and the chiral purity is high.

A facile approach to chiral 1,4-benzodioxane toward the syntheses of doxazosin, prosympal, piperoxan, and dibozane

The process describes the concise synthesis of (R/S)-enantiomers of doxazosin, an antidepressant drug and α-adrenergic receptor antagonists like prosympal, piperoxan, and dibozane in practical yields from easily available (R)-2,3-O-cyclohexylidene-d-glyce

Absolute configuration of glycerol derivatives. 4. Synthesis and pharmacological activity of chiral 2 alkylaminomethylbenzodioxans, competitive α adrenergic antagonists

The optical isomers of α-adrenergic receptor antagonists prosympal (2), piperoxan (3), and dibozane (4) were prepared by methods establishing the absolute configuration of each. (2S)-3-(2'-Hydroxyphenoxy)-1,2-propanediol ditosylate (10) was prepared from (2R)-3-tosyloxy-1,2-propanediol acetonide (6). Intramolecular displacement afforded (2S)-tosyloxymethylbenzodioxan [(2R)-11]. Reaction of (2R)-11 with the appropriate amine (diethylamine, piperidine, or piperazine) afforded the 2S isomers of 2, 3, and 12, respectively. Reaction of (2S)-12 with (2R)-11 afforded the SS isomer of 4. Reaction of (2S)-3-benzoloxy-1,2-propanediol ditosylate (14) with catechol (NaOMe) afforded (2R)-benzyloxymethylbenzodioxan (15). Subjecting 15 to hydrogenolysis, tosylation, and displacement with the appropriate amine afforded 2R isomers of 2, 3, and 12. Reaction of (2R)-12 with (2S)-11 afforded (RR)-4. Reaction of (2R)-12 with (2R)-11 afforded meso-4. The S isomers were more effective antagonists to the α-adrenergic response of methoxamine-induced contraction of rabbit aortic strips by twofold in 2 and 18-19-fold in 3 and 4. meso-4 was as effective as the SS isomer of 4. The results are interpreted in terms of a similar conformational distribution of aminoalkyl, oxygen, and aromatic functional groups of the (S)-benzodioxans and (R)-epinephrine.