85240-28-4

Upstream product

• 85240-27-3 1L-(1,3,4/2,6)-1,2,3-tri-O-acetyl-4-<(benzyloxycarbonyl)amino>-6-C-(p-tolylsulfonyloxymethyl)-1,2,3-cyclohexanetriol 
• 32780-32-8 validamine 
• 75-36-5 acetyl chloride 
• 501-53-1 benzyl chloroformate 
• 85240-26-2 N-(benzyloxycarbonyl)-7-O-(p-tolylsulfonyl)validamine 
• 85281-05-6 N-(benzyloxycarbonyl)validamine 

Downstream Products

• 85240-29-5 1L-(1R)-(1,3,4/2)-tri-O-acetyl-4-<(benzyloxycarbonyl)amino>-6-methylene-1,2,3-cyclohexanetriol 
• 90865-96-6 epivaliolamine 
• 89876-10-8 (1R)-(1(CH2OH),2,4,5/1,3)-2,3,4-tri-O-acetyl-5-<(benzyloxycarbonyl)amino>-1-C-(hydroxymethyl)-1,2,3,4-cyclohexanetetrol 
• 85240-30-8 1L(1R)-(1,3,4/2)-<(benzyloxycarbonyl)amino>-6-methylene-1,2,3-cyclohexanetriol 
• 83465-22-9 (1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane 

Relevant academic research and scientific papers

Synthesis method of valiolamine key intermediate

The invention relates to a synthesis method of a valiolamine key intermediate IV. According to the method, valiolamine is used as a raw material to prepare the key intermediate IV through amino protection, 4-site dydroxymethyl iodideo reaction, 1,2,3-site three-hydroxyl protection, hydrogen iodide removal and double-bond forming; the key intermediate IV can be used for synthesizing valiolamine.

STEREOSELECTIVE CONVERSION OF VALIENAMINE AND VALIDAMINE INTO VALIOLAMINE

Methods are described for the stereoselective conversion of valienamine (2) and validamine (3) into valiolamine (1a), a new pseudo-amino sugar isolated from the fermentation broth of Streptomyces hygroscopicus subsp. limoneus and which is a stronger α-D-glucosidase inhibitor than 2 and 3.Treatment of the acyclic carbamates (4) of 2 with halogenation reagents led to ring closure to afford the halo cyclic carbamates (6), which were reductively dehalogenated and then hydrolyzed to give 1a.Similar treatment of the exomethylene acyclic carbamate (12), derived from 3 via 8-11, resulted in the formation of halo cyclic carbamates (14a,b), which were converted into 1a.The synthesis of epivaliolamine (1b), the C-1 epimer of 1a, starting from 2 and 3, is also described.