6-(Hydroxymethyl)piperidine-2,3,4,5-tetrol

Base Information

• Chemical Name: 6-(Hydroxymethyl)piperidine-2,3,4,5-tetrol
• CAS No.: 138382-48-6
• Molecular Formula: C6H13NO5
• DSSTox Substance ID: DTXSID90391090
• Wikidata: Q82188318
• ChEMBL ID: CHEMBL35691

Synonyms:Antibiotic R-468;Substance SF-425;D-Glucopyranose, 5-amino-5-deoxy-;138382-48-6;2,3,4,5-Piperidinetetrol, 6-(hydroxymethyl)-;BRN 5246306;R 468;U 51640;CHEMBL35691;SCHEMBL11239684;DTXSID90391090

Chemical Property of 6-(Hydroxymethyl)piperidine-2,3,4,5-tetrol

Chemical Property:

• XLogP3: -2.9
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 179.07937252
• Heavy Atom Count: 12
• Complexity: 155

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(N1)O)O)O)O)O

Technology Process of 6-(Hydroxymethyl)piperidine-2,3,4,5-tetrol

There total 3 articles about 6-(Hydroxymethyl)piperidine-2,3,4,5-tetrol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4R,5S)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (138319-95-6) → (-)-galactostatin (15218-38-9,19130-94-0,62362-40-7,107537-94-0,108147-56-4,109718-63-0,109718-64-1,109718-65-2,121251-50-1,126575-57-3,138382-48-6,149406-05-3)

Guidance literature:

With trifluoroacetic acid; for 0.5h; Ambient temperature;

DOI:10.1039/c39910001576

Reference yield:

5-amino-5-deoxy-D-glucose-1-sulfonic acid (81703-56-2) → nojirimycin (15218-38-9,19130-94-0,62362-40-7,107537-94-0,108147-56-4,109718-63-0,109718-64-1,109718-65-2,121251-50-1,126575-57-3,138382-48-6,149406-05-3)

Guidance literature:

With Dowex 1x2; water; for 0.5h; Ambient temperature; pH 8-10;

Reference yield:

5-amino-5-deoxy-L-altropyranose hydrogensulfite adduct (78698-43-8,81703-56-2,91384-36-0,91384-37-1,109784-32-9,109784-33-0,109784-34-1,109784-35-2,114417-84-4,126575-58-4,130979-29-2,149406-06-4,149406-07-5) → 5-amino-5-deoxy-L-altropyranose (15218-38-9,19130-94-0,62362-40-7,107537-94-0,108147-56-4,109718-63-0,109718-64-1,109718-65-2,121251-50-1,126575-57-3,138382-48-6,149406-05-3)

Guidance literature:

With barium dihydroxide; for 1h; Ambient temperature; pH >/= 8;

DOI:10.1016/S0008-6215(00)90138-1

upstream raw materials:

5-amino-5-deoxy-D-glucose-1-sulfonic acid

(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4R,5S)-5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

5-amino-5-deoxy-L-altropyranose hydrogensulfite adduct

Downstream raw materials:

nojirimycin-δ-lactam

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