Methyl 1,2,3,4-tetra-O-acetyl-alpha-L-idopyranuronate

Base Information

• Chemical Name: Methyl 1,2,3,4-tetra-O-acetyl-alpha-L-idopyranuronate
• CAS No.: 108032-41-3
• Molecular Formula: C15H20O11
• Molecular Weight: 376.317
• DSSTox Substance ID: DTXSID30483620
• Nikkaji Number: J344.081H
• Wikidata: Q82321076
• Mol file: 108032-41-3.mol

Synonyms:108032-41-3;Methyl 1,2,3,4-Tetra-O-acetyl-|A-L-iduronate;METHYL 1,2,3,4-TETRA-O-ACETYL-ALPHA-L-IDOPYRANURONATE;methyl (2R,3S,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxane-2-carboxylate;Methyl 1,2,3,4-tetra-O-acetyl-a-L-idopyranuronate;DTXSID30483620;A934194;W-200773;Methyl 1,2,3,4-Tetra-O-acetyl-?-L-idopyranuronate

Chemical Property of Methyl 1,2,3,4-tetra-O-acetyl-alpha-L-idopyranuronate

Chemical Property:

• Melting Point: 120-122°C
• PSA: 140.73000
• LogP: -0.75750
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 376.10056145
• Heavy Atom Count: 26
• Complexity: 584

Purity/Quality:

97% ^*data from raw suppliers

Methyl1,2,3,4-Tetra-O-acetyl-α-L-idopyranuronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@@H](O[C@H]([C@@H]1OC(=O)C)OC(=O)C)C(=O)OC)OC(=O)C
• Uses: Methyl 1,2,3,4-Tetra-O-acetyl-α-L-idopyranuronate is used in the synthesis of L-iduronic acid derivatives from D-glucuronic acid analogs. A useful synthetic intermdiate for carbohydrate synthesis.

Technology Process of Methyl 1,2,3,4-tetra-O-acetyl-alpha-L-idopyranuronate

There total 17 articles about Methyl 1,2,3,4-tetra-O-acetyl-alpha-L-idopyranuronate 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: 92.0%

methyl D-glucopyranuronate (82228-14-6) + acetic anhydride (108-24-7) → methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃; for 5h;

DOI:10.1002/ejoc.200500555

Reference yield: 77.0%

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetic anhydride (108-24-7) → methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3)

Guidance literature:

D-glucurono-6,3-lactone; With sodium hydroxide; In methanol; at 20 ℃; for 24h; Inert atmosphere;

acetic anhydride; With pyridine; at 10 - 20 ℃; for 4h; Inert atmosphere;

Reference yield: 77.0%

methanol (67-56-1) + D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) + acetic anhydride (108-24-7) → methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3)

Guidance literature:

methanol; D-glucurono-6,3-lactone; With sodium hydroxide; at 20 ℃; for 24h; Inert atmosphere;

acetic anhydride; With pyridine; at 10 - 20 ℃; for 4h;

upstream raw materials:

methyl D-glucopyranuronate

acetic anhydride

D-(+)-glucuronic acid γ-lactone

D-glucurono-6,3-lactone

Downstream raw materials:

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester

2,3,4-tri-O-acetyl-β-D-glucopyranosylamine uronic acid methyl ester

methyl (phenyl 2,3-di-O-acetyl-4-deoxy-1-thio-α-L-threo-hex-4-enopyranosid)uronate