1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose

Base Information

• Chemical Name: 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose
• CAS No.: 67817-30-5
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID50510700
• Wikidata: Q72504459
• Mol file: 67817-30-5.mol

Synonyms:67817-30-5;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose;1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-A-D-GALACTOPYRANOSE;[(2R,3R,4R,5R,6R)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-|A-D-galactopyranose;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose ,;MFCD01076182;QKGHBQJLEHAMKJ-RGDJUOJXSA-;DTXSID50510700;AC6587;AKOS015919013;T1731;W-203505;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy--D-galactopyranose;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-.alpha.-D-galactopyranose;InChI=1/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1

Chemical Property of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose

Chemical Property:

• Melting Point: 120.0 to 127.0 °C
• PSA: 164.18000
• LogP: -0.16744
• Storage Temp.: Refrigerator
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 373.11212919
• Heavy Atom Count: 26
• Complexity: 617

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-a-D-galactopyranose ^*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)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@@H]([C@@H]([C@H]([C@H](O1)OC(=O)C)N=[N+]=[N-])OC(=O)C)OC(=O)C

Technology Process of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose

There total 13 articles about 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-A-D-galactopyranose 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:

acetic anhydride (108-24-7) + 2-deoxy-2-azidogalactopyranose (68733-26-6) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose (67817-30-5) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl acetate (68733-19-7)

Guidance literature:

With pyridine; dmap; optical yield given as %de;

DOI:10.1021/ja902607a

Reference yield:

D-(+)-galactosamine hydrochloride (1772-03-8,4710-95-6,6730-09-2,14131-59-0,14131-62-5,14131-63-6,14131-65-8,14131-67-0,14257-79-5,19124-46-0,20706-90-5,91673-92-6) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose (67817-30-5) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl acetate (68733-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate / methanol / 20 °C

2: pyridine; dmap

With pyridine; dmap; imidazole-1-sulfonyl azide hydrochloride; potassium carbonate; copper(II) sulfate; In methanol;

DOI:10.1021/ja902607a

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl nitrate (68733-06-2) → 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranose (67817-30-5)

Guidance literature:

With sodium acetate; In water; acetic acid;

upstream raw materials:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate

potassium thioacetate

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose

triacetyl-D-galactal

Downstream raw materials:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl bromide

ethyl p-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyloxy)cinnamate

(E)-3-[4-((2R,3R,4R,5R,6R)-3-Amino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester

(E)-3-[4-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-phenyl]-acrylic acid tert-butyl ester