128741-75-3

Usage

Chemical Properties

White Foam

Uses

Intermediate in the preparation of Kifunensine,

Upstream product

• 553-90-2 Dimethyl oxalate 
• 149819-14-7 (2R,3R,4R,5R)-5-amino-2,3:4,6-di(isopropylidenedioxy)hexanol 
• 1054645-70-3 N-[(4R,5R)-4-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-[1,3]dioxan-5-yl]-oxalamic acid methyl ester 
• 471-47-6 oxamic acid 
• 118464-47-4 6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-gulonolactone 
• 118464-49-6 (3S,4S,5R)-5-[(1R)-1-azido-2-tert-butyldimethylsilanyloxyethyl]-3,4-isopropylidenedioxytetrahydrofuran-2-one 
• 94840-08-1 2,3-O-isopropylidene-L-gulono-γ-lactone 
• 7306-64-1 2,3:5,6-di-O-isopropylidene-L-gulonolactone 
• 1128-23-0 L-gulono-1,4-lactone 
• 118464-48-5 Trifluoro-methanesulfonic acid (S)-2-(tert-butyl-dimethyl-silanyloxy)-1-((3aS,4S,6aS)-2,2-dimethyl-6-oxo-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-ethyl ester 
• 90-76-6 D-mannosamine 
• 4710-95-6 D-mannosamine hydrochloride 
• 136492-89-2 6-O-tert-Butyldiphenylsilyl-2-deoxy-2-oxamoylamino-D-mannose 
• 128741-73-1 6-O-tert-Butyldiphenylsilyl-2-deoxy-2-oxamoylamino-D-mannitol 

Downstream Products

• 136492-90-5 anti-5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose 2,4-dinitrophenylhydrazone 
• 136492-91-6 syn-5-Deoxy-2,3:4,6-di-O-isopropylidene-5-oxamoylamino-D-mannose 2,4-dinitrophenylhydrazone 
• 122623-76-1 C₁₄H₂₀N₂O₆ 
• 109944-15-2 8a-epi-kifunensine 
• 134234-43-8 (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dion-4-azaindolizidine 
• 109944-15-2 kifunensine 
• 872038-13-6 (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine 

Relevant academic research and scientific papers

Synthesis method of mannosidase inhibitor Kifunensine

The invention provides a synthesis method of mannosidase inhibitor Kifunensine. L-gulonic acid-gamma-lactone, which is cheap and easily available, is taken as an initial raw material to efficiently obtain the Kifunensine through multi-step chemical conversion, the overall yield of the reaction is high, reagents used in the process are cheap and easily available, and multiple steps in the synthesis process can be fed by a one-pot method, so that the operation is simple and convenient, and the method has a better industrial prospect.

A practical synthesis of kifunensine analogues as inhibitors of endoplasmic reticulum α-mannosidase I

A practical synthesis of the potent class I α-mannosidase inhibitor kifunensine (1) beginning from the inexpensive and readily available starting material L-ascorbic acid (15) is described. The protected amino-alcohol ((2R,3R,4R,5R)-5-amino-2,3:4,6-diisop

Microbial oxidation of aromatics in enantiocontrolled synthesis. 2.1 rational design of aza sugars (endo-nitrogenous). Total synthesis of (+)-kifunensine, mannojirimycin, and other glycosidase inhibitors

A general method of synthesis for lactones and lactams related to carbohydrates has been developed that relies on the biocatalytic generation of 1-chloro-2,3-dihydroxycyclohexa-4,6-diene (1), obtained in excellent yield by fermentation of chlorobenzene with Pseudomonasputida 39D, followed by further functionalization to nitrogen-substituted cyclitols. These amino or azido cyclitols of type 15 are then subjected to controlled ozonolysis, which yields either lactones such as 27 or lactams containing five-membered (28) or six-membered (20 and 23) rings. Such compounds are useful intermediates for the preparation of aza sugars. Mannojirimycin (8a) has been synthesized in seven steps from chlorobenzene. Kifunensine (7) has been prepared in 11 steps from chlorobenzene following an intersection with Hashimoto's procedure. Full experimental and spectral details are provided for all compounds. The potential of this general method and implications of the disclosed design features in the field of amino sugar and aza sugar synthesis are indicated.

Total Synthesis of (+)-Kifunensine, a Potent Glycosidase Inhibitor

(+)-Kifunensine, a potent inhibitor of mannosidase I, has been synthesized in 13 steps from chlorobenzene by microbial oxygenation with Pseudomonas putida 39D and stereocontrolled peripheral functionalization of cis-3-chlorocylohexa-3,5-dienediol 3.

Synthesis of kifunensine, an immunomodulating substance isolated from a microbial source

Kifunensine (1), a novel immunomodulator isolated from an actinomycete, was enantiospecifically synthesized from D-mannosamine via a double cyclization of the oxamide-aldehyde precursor with ammonia as a key step. The absolute stereochemistry of natural kifunensine was confirmed to be the D form.

SYNTHESIS OF KIFUNENSINE, AN IMMUNOMODULATING SUBSTANCE ISOLATED FROM MICROBIAL SOURCE

A synthesis of kifunensine (1) has been achieved by a route involving, as a key step, a double cyclization of aldehyde 3 with ammonia.