85281-05-6

Upstream product

• 32780-32-8 validamine 
• 501-53-1 benzyl chloroformate 
• 32780-31-7 DL-validamine hydrochloride 
• 64589-26-0 (+/-)-<(1,3/2,4,5)-5-acetamido-2,3,4-triacetoxycyclohexyl>-methyl acetate 

Downstream Products

• 85240-30-8 1L(1R)-(1,3,4/2)-<(benzyloxycarbonyl)amino>-6-methylene-1,2,3-cyclohexanetriol 
• 85240-28-4 1L-(1,3,4/2,6)-1,2,3-tri-O-acetyl-4-<(benzyloxycarbonyl)amino>-6-C-(iodomethyl)-1,2,3-cyclohexanetriol 
• 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 
• 85240-29-5 1L-(1R)-(1,3,4/2)-tri-O-acetyl-4-<(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 
• 89859-87-0 (1R)-(1,3,4/2,6)-1-O-benzoyl-2,3-O-cyclohexylidene-4-<(benzyloxycarbonyl)amino>-6-C-(bromomethyl)-1,2,3-cyclohexanetriol 
• 89859-88-1 (1R)-(1,3,4/2,6)-1-O-benzoyl-2,3-O-cyclohexylidene-4-<(benzyloxycarbonyl)amino>-6-C-methyl-1,2,3-cyclohexanetriol 
• 89859-86-9 (1R)-(1,3,4/2,6)-1-O-benzoyl-4-<(benzyloxycarbonyl)amino>-6-C-(bromomethyl)-1,2,3-cyclohexanetriol 
• 89859-90-5 (2R)-(2,6/3,4)-2,3-O-cyclohexylidene-4-<(benzyloxycarbonyl)amino>-2,3-dihydroxy-6-methylcyclohexanone 
• 89859-89-2 (1R)-(1,3,4/2,6)-2,3-O-cyclohexylidene-4-<(benzyloxycarbonyl)amino>-6-C-methyl-1,2,3-cyclohexanetriol 
• 89859-47-2 (1R)-(1,3,4/2,6)-1,7-O-benzylidene-4-<(benzyloxycarbonyl)amino>-6-C-(hydroxymethyl)-1,2,3-cyclohexanetriol 
• 86195-51-9 (-)-validamine hydrochloride 
• 32780-31-7 (+)-validamine hydrochloride 
• 73410-97-6 1D-2-O-β-D-glucopyranosyl-(1,3,4/2,6)-4-amino-6-hydroxymethyl-1,2,3-cyclohexanetriol 

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.

Volt-voglibose intermediate and its preparation method

The invention relates to a voglibose intermediate as shown in the following formula V and a preparation method of the voglibose intermediate and also relates to a preparation method of a voglibose intermediate 1L(1S)-(1(OH), 2, 4, 5/1, 3)-5-amino-1-C-(hydroxymethyl)-1, 2, 3, 4-tetrahydroxycyclohexane. The method comprises the steps: with a validamycin fermentation byproduct 1L(1, 3, 4/2)-4-amino-6-hydroxymethyl-1, 2, 3-trihydroxycyclohexane as a raw material, carrying out amino protection, elimination, epoxidation, hydrolysis and deprotection reaction to obtain valiolamine. Compared with the traditional synthesis method, the method disclosed by the invention is few in synthesis step, little in pollution due to the adoption of a recyclable efficient catalyst, simple in operation and stable in yield.

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.

SYNTHESIS OF β-D-GLUCOPYRANOSYLVALIDAMINE: 2-O-β-D-GLUCOPYRANOSYL-1L-(1,3,4/2,6)-4-AMINO-6-HYDROXYMETHYL-1,2,3-CYCLOHEXANETRIOL

β-D-Glucopyranosylvalidamine (1a), the structure of which was assigned to the degradation product of validamycin A, was synthesized by condensation of a protected validamine (8) with acetobromoglucose, followed by deblocking.Unexpectedly, 1a was found not to be identical with an authentic sample derived from the antibiotic