4-O-alpha-D-Glucopyranosylmoranoline

Base Information

• Chemical Name: 4-O-alpha-D-Glucopyranosylmoranoline
• CAS No.: 80312-32-9
• Molecular Formula: C12H23NO9
• Molecular Weight: 325.3123
• DSSTox Substance ID: DTXSID701135748
• Metabolomics Workbench ID: 49743
• Nikkaji Number: J410.712H
• Wikidata: Q27139052
• Mol file: 80312-32-9.mol

Synonyms:1-deoxy-nojirimycin 4-O-alpha-D-glucopyranose;1-deoxynojirimycin 4-O-alpha-D-glucopyranose;4-O-alpha-D-glucopyranosylmoranoline;4-O-glucopyranosylmoranoline;MOR-502

Chemical Property of 4-O-alpha-D-Glucopyranosylmoranoline

Chemical Property:

• Vapor Pressure: 3.06E-14mmHg at 25°C
• Melting Point: 189-192oC
• Boiling Point: 546.9°Cat760mmHg
• PKA: 12.90±0.70(Predicted)
• Flash Point: 284.6°C
• PSA: 172.10000
• Density: 1.67g/cm³
• LogP: -4.81380
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Methanol (Very Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -4.5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 325.13728131
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

98%Min ^*data from raw suppliers

4-O-α-D-Glucopyranosylmoranoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(N1)CO)OC2C(C(C(C(O2)CO)O)O)O)O)O
• Isomeric SMILES: C1[C@@H]([C@H]([C@@H]([C@H](N1)CO)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O)O
• Uses: An a-glucosidase inhibitor. May also prove to be an effective oral anti-diabetic agent An α-glucosidase inhibitor. May also prove to be an effective oral anti-diabetic agent.

Technology Process of 4-O-alpha-D-Glucopyranosylmoranoline

There total 15 articles about 4-O-alpha-D-Glucopyranosylmoranoline 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: 71.0%

2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-deoxynojirimycin → 4-O-α-D-glucopyranosyl-(1->4)-1-deoxynojirimycin (80312-32-9)

Guidance literature:

With hydrogenchloride; palladium on activated charcoal; hydrogen; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201801461

Reference yield: 30.0%

(2S,3R)-4-((2R,4aR,6R,7R,8R,8aS)-7,8-Dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2,3,6-trihydroxy-5-oxo-hexanal → 4-O-α-D-glucopyranosyl-(1->4)-1-deoxynojirimycin (80312-32-9)

Guidance literature:

With ammonium hydroxide; hydrogen; palladium dihydroxide; In water; for 96h; under 760 Torr;

DOI:10.1016/j.carres.2004.07.022

Reference yield:

4-O-α-D-glucopyranosyl-N-(benzyloxycarbonyl)-1-deoxynojirimycin → 4-O-α-D-glucopyranosyl-(1->4)-1-deoxynojirimycin (80312-32-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; acetic acid; for 16h; under 760 Torr;

DOI:10.1016/0008-6215(94)84091-1

upstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

(2R,4aR,6R,7R,8R,8aS)-6-((2S,3S,4R,5R)-4,5-Dihydroxy-2-iodomethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

methyl (5R,S)-2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-5,6-anhydro-5-hydroxy-α,β-D-xylo-hexopyranoside

methyl 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl-(1->4)-2,3-di-O-acetyl-α,β-D-xylo-hex-5-enopyranosyde

Downstream raw materials:

(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-1-(4-phenoxy-butyl)-piperidin-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

4-O-α-D-glucopyranosyl-N-(3-phenylpropyl)moranoline

(2S,3R,4S,5S,6R)-2-((2R,3R,4R,5S)-1-Benzyl-4,5-dihydroxy-2-hydroxymethyl-piperidin-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

(2S,3R,4S,5S,6R)-2-[(2R,3R,4R,5S)-4,5-Dihydroxy-2-hydroxymethyl-1-(4-methyl-benzyl)-piperidin-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

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