(2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Base Information

• Chemical Name: (2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate
• CAS No.: 3006-60-8
• Molecular Formula: C16H23 N O10
• Molecular Weight: 389.359
• Hs Code.: 2940006000
• DSSTox Substance ID: DTXSID201162611
• Nikkaji Number: J2.503.326D
• Mol file: 3006-60-8.mol

Synonyms:3006-60-8;(2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate;beta-D-Galactosamine pentaacetate;2-ACETAMIDO-1,3,4,6-TETRA-O-ACETYL-2-DEOXY-B-D-GALACTOPYRANOSE;[(2R,3R,4R,5R,6S)-5-acetamido-3,4,6-triacetyloxyoxan-2-yl]methyl acetate;MFCD00214297;C16H23NO10;2-(Acetylamino)-2-deoxy-beta-D-galactopyranose 1,3,4,6-tetraacetate;(2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)-tetrahydro-2H-pyran-2,4,5-triyl triacetate;AMY346;SCHEMBL2288412;DTXSID201162611;AKOS015841027;AKOS015902933;CS-W005729;DS-4512;(2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyltriacetate;BP-31130;EN300-7356985;A876317;W-202246;2-Acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-beta-D-glucopyranose;2-Acetamido-1,3,4,6-tetrakis-(O-acetyl)-2-deoxy-D-galactospyranose;Acetyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-galactopyranoside;beta-D-Galactopyranose, 2-(acetylamino)-2-deoxy-, 1,3,4,6-tetraacetate;[(2R,3R,4R,5R,6S)-3,4,6-TRIS(ACETYLOXY)-5-ACETAMIDOOXAN-2-YL]METHYL ACETATE;1-O,3-O,4-O,6-O-Tetraacetyl-2-(acetylamino)-2-deoxy-beta-D-galactopyranose;acetic acid (2S,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yl ester

Chemical Property of (2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

Chemical Property:

• Vapor Pressure: 2.53E-11mmHg at 25°C
• Melting Point: 234-236℃
• Boiling Point: 530.2°C at 760 mmHg
• PKA: 13.41±0.70(Predicted)
• Flash Point: 274.4°C
• PSA: 143.53000
• Density: 1.30
• LogP: -0.40350
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility.: Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly, Heated), Methanol (Sli
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 389.13219593
• Heavy Atom Count: 27
• Complexity: 604

Purity/Quality:

98% ^*data from raw suppliers

2-Acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-b-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
• Uses: (2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl Triacetate is used to synthesize selenium monosaccharide as metabolic biomarker.

Technology Process of (2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-triyl triacetate

There total 140 articles about (2S,3R,4R,5R,6R)-3-Acetamido-6-(acetoxymethyl)tetrahydro-2H-pyran-2,4,5-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: 95.0%

2-amino-2-deoxy-D-glucose hydrochloride + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine; at 20 ℃; Cooling with ice;

DOI:10.1080/07328303.2014.996290

Reference yield: 90.0%

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride (5432-46-2,10034-19-2,10034-20-5,34948-62-4,110253-00-4,1191127-63-5) + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine;

DOI:10.1002/ejoc.201200062

Reference yield: 88.0%

N-acetyl-D-glucosamine (14131-68-1) + acetic anhydride (108-24-7) → 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3)

Guidance literature:

With pyridine; at 20 ℃; for 29.5h;

upstream raw materials:

acetic anhydride

2-amino-2-deoxy-D-idose; hydrochloride

1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride

D-(+)-glucosamine hydrochloride

Downstream raw materials:

[1]naphthyl-(tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranoside)

2-acetylamino-1,1-diphenyl-1,2-dideoxy-D-glucitol

p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester

Refernces

• 1、 Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan. "Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents". . . Retrieved 2021/12/30.
• 2、 Morelli, Laura,Legnani, Laura,Ronchi, Silvia,Confalonieri, Laura,Imperio, Daniela,Toma, Lucio,Compostella, Federica. "2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study". . . Retrieved 2021/08/26.