D-Mannojirimycin

Base Information

• Chemical Name: D-Mannojirimycin
• CAS No.: 62362-40-7
• Molecular Formula: C6H13NO5
• Molecular Weight: 179.171
• Hs Code.: 2922399090
• Mol file: 62362-40-7.mol

Synonyms:5-AMINO-5-DEOXY-D-GALACTOPYRANOSIDE;

Chemical Property of D-Mannojirimycin

Chemical Property:

• PSA: 116.17000
• LogP: -2.55470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-Mannojirimycin

There total 7 articles about D-Mannojirimycin 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-D-mannopyranose hydrogensulfite

5-amino-1-O-benzyl-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranose

Downstream raw materials:

nojirimycin-δ-lactam

Refernces

• 1、 Hudlicky, Tomas,Rouden, Jacques,Luna, Hector,Allen, Scott. "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". . p. 5099 - 5107. Retrieved 2007/10/02.
• 2、 Dondoni, Alessandro,Merino, Pedro,Perrone, Daniela. "Stereocontrolled Total Synthesis of Galactostasin from Serine". . p. 1576 - 1578. Retrieved 2007/10/02.