2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine
• CAS No.: 108342-87-6
• Molecular Formula: C26H45NO9
• Molecular Weight: 515.645
• Hs Code.: 29329990
• European Community (EC) Number: 621-990-6
• DSSTox Substance ID: DTXSID10428796
• Nikkaji Number: J688.134C
• Mol file: 108342-87-6.mol

Synonyms:108342-87-6;2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine;2,3,4,6-TETRA-O-PIVALOYL-D-GALACTOPYRANOSYLAMINE;2,3,4,6-Tetra-O-pivaloyl-|A-D-galactopyranosylamine;2,3,4,6-Tetra-O-pivaloyl-b-D-galactopyranosyl amine;[(2R,3S,4S,5R,6R)-6-amino-3,4,5-tris(2,2-dimethylpropanoyloxy)oxan-2-yl]methyl 2,2-dimethylpropanoate;[(2R,3S,4S,5R,6R)-6-AMINO-3,4,5-TRIS[(2,2-DIMETHYLPROPANOYL)OXY]OXAN-2-YL]METHYL 2,2-DIMETHYLPROPANOATE;SCHEMBL2224141;DTXSID10428796;(2R,3R,4S,5S,6R)-2-Amino-6-((pivaloyloxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate);b-D-Galactopyranosylamine, 2,3,4,6-tetrakis(2,2-dimethylpropanoate);AKOS015841100;AS-72209;D95071;2,3,4,6-tetra-O-pivaloyl-beta-D-galacto-pyranosyl;W-200782;Ethyl 2-hydroxy-6-methyl-4-(trifluoromethyl)nicotinate;2,3,4,6-Tetra-O-pivaloyl- beta -D-galactopyranosylamine;2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine, 99%;(2R,3R,4S,5S,6R)-2-amino-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3,4,5-triyl tris(2,2-dimethylpropanoate)

Chemical Property of 2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine

Chemical Property:

• Vapor Pressure: 2.9E-11mmHg at 25°C
• Melting Point: 92-95 °C(lit.)
• Refractive Index: 1.488
• Boiling Point: 528.692 °C at 760 mmHg
• PKA: 6.96±0.70(Predicted)
• Flash Point: 75.917 °C
• PSA: 140.45000
• Density: 1.117 g/cm³
• LogP: 3.83330
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 13
• Exact Mass: 515.30943201
• Heavy Atom Count: 36
• Complexity: 824

Purity/Quality:

98%Min ^*data from raw suppliers

2,3,4,6-Tetra-O-pivaloyl-b-D-galactopyranosyl amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OCC1C(C(C(C(O1)N)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• Isomeric SMILES: CC(C)(C)C(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)N)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• Uses: 2,3,4,6-Tetra-O-pivaloyl-D-galactopyranosylamine (CAS# 108342-87-6) is a useful building block used in the diastereoselective synthesis of adjacent P,C-stereogenic β-N-glycosidic linked α-aminophosphinates.

Technology Process of 2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine

There total 7 articles about 2,3,4,6-Tetra-O-pivaloyl-beta-D-galactopyranosylamine 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: 91.0%

2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide (108342-86-5) → tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6)

Guidance literature:

With triphenylphosphine; In tetrahydrofuran; water; at 20 ℃; for 20h;

DOI:10.1016/j.tet.2018.01.007

Reference yield: 79.0%

N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-p-anisamide (606092-33-5) → tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6)

Guidance literature:

N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-p-anisamide; With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20 ℃; for 4h;

With ammonia; silver trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 18h;

DOI:10.1002/anie.200351351

Reference yield: 25.0%

N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)acetamide (606092-30-2) → tetra-O-pivaloyl-β-D-galactopyranosylamine (108342-87-6)

Guidance literature:

N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)acetamide; With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20 ℃;

With ammonia; silver trifluoromethanesulfonate; In acetonitrile; at 20 ℃;

DOI:10.1002/anie.200351351

upstream raw materials:

2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl azide

N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)acetamide

N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-p-anisamide

1,2,3,4,6-penta-O-pivaloyl-β-D-galactopyranose

Downstream raw materials:

N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(R)-α-amino-5-cyano-pentanoic acid-N'-tert-butyl-amide

N-formyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)-(S)-α-amino-5-cyano-pentanoic acid-N'-tert-butyl-amide

4-methyl-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine

4-fluoro-N-(2,3,4,6-tetra-O-pivaloyl-β-D-galactopyranosyl)benzylideneamine

Refernces

• 1、 Hryniewicka, Agnieszka,?otowski, Zenon,Seroka, Barbara,Witkowski, Stanis?aw,Morzycki, Jacek W.. "Synthesis of a cisplatin derivative from lithocholic acid". . p. 5392 - 5398. Retrieved 2018/02/12.
• 2、 Pleuss, Norbert,Kunz, Horst. "N-glycosyl amides as glycosyl donors in stereoselective glycosylation reactions". . p. 122 - 130. Retrieved 2007/10/03.