(2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 58484-22-3
• Molecular Formula: C₁₄H₂₁NO₉
• Molecular Weight: 347.322
• DSSTox Substance ID: DTXSID50464577
• Nikkaji Number: J1.663.958C
• Wikidata: Q72504477
• Mol file: 58484-22-3.mol

Synonyms:58484-22-3;(2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-aminooxan-2-yl]methyl acetate;2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosylamine;LMVYBLMOENOGGK-MBJXGIAVSA-N;SCHEMBL5497115;DTXSID50464577;AKOS016011285;(2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyltriacetate;A869433;2,3,4,6-Tetra-O-acetyl-|A-D-galactopyranosylamine;2,3,4,6-Tetra-O-acetyl-b-D-galactopyranosylamine

Chemical Property of (2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

• Melting Point: 120-122℃
• Boiling Point: 411.6±45.0 °C(Predicted)
• PKA: 7.37±0.70(Predicted)
• PSA: 140.45000
• Density: 1.30
• LogP: -0.27150
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 347.12163125
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

99% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)N)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)N)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosylamine is used in the preparation of organo-selenium glycosides and disaccharides which target multiple kinases and are capable of inhibiting cancer progression to metastases.

Technology Process of (2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 31 articles about (2R,3S,4S,5R,6R)-2-(Acetoxymethyl)-6-aminotetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 100.0%

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate (13992-25-1) → 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine (41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1039/b201296k

Reference yield: 100.0%

(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-azidotetrahydro-2H-pyran-3,4,5-triyl triacetate (13992-26-2) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylamine (41355-50-4,51642-81-0,70128-27-7,70145-20-9,94482-21-0,98300-76-6,58484-22-3)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1039/b201296k

Reference yield: 84.0%

2,3,4,6-tetra-O-acetyl-N-(fluoren-9-ylmethoxycarbonyl)-β-D-glucopyranosylamine (152844-02-5) → 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine (41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6)

Guidance literature:

With piperidine; In tetrahydrofuran; for 0.166667h; Ambient temperature;

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine hydrobromide

2,3,4,6-tetra-O-acetyl-N-(fluoren-9-ylmethoxycarbonyl)-β-D-glucopyranosylamine

1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide

Downstream raw materials:

N-Formyl-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(S)-phenylglycine-N'-tert-butyl-amide

N-Formyl-N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(R)-phenylglycine-N'-tert-butyl-amide

N-[(R)-3-(benzyloxy)tetradecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine

N-[3-benzyloxy-2,2-difluorotetradecanoyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosylamine

Refernces

• 1、 Sr?an, Laura,Ziegler, Thomas. "Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations". supporting information. p. 888 - 894. Retrieved 2020/05/18.
• 2、 Galan, M. Carmen,Ghirardello, Mattia,Ledru, Helene,Sau, Abhijit. "Chemo-selective Rh-catalysed hydrogenation of azides into amines". supporting information. . Retrieved 2020/02/18.