1,2,3-Tri-o-acetyl-6-deoxy-4-o-(2,3,4,6-tetra-o-acetylhexopyranosyl)hexopyranose

Base Information

• Chemical Name: 1,2,3-Tri-o-acetyl-6-deoxy-4-o-(2,3,4,6-tetra-o-acetylhexopyranosyl)hexopyranose
• CAS No.: 28810-04-0
• Molecular Formula: C₂₆H₃₆O₁₇
• Molecular Weight: 620.562
• NSC Number: 105393
• DSSTox Substance ID: DTXSID10295768
• Mol file: 28810-04-0.mol

Synonyms:28810-04-0;NSC105393;1,2,3-tri-o-acetyl-6-deoxy-4-o-(2,3,4,6-tetra-o-acetylhexopyranosyl)hexopyranose;DTXSID10295768;NSC-105393

Chemical Property of 1,2,3-Tri-o-acetyl-6-deoxy-4-o-(2,3,4,6-tetra-o-acetylhexopyranosyl)hexopyranose

Chemical Property:

• Vapor Pressure: 3.94E-16mmHg at 25°C
• Boiling Point: 637.1°Cat760mmHg
• Flash Point: 265.1°C
• Density: 1.34g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 17
• Exact Mass: 620.19524968
• Heavy Atom Count: 43
• Complexity: 1070

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C)OC2C(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 1,2,3-Tri-o-acetyl-6-deoxy-4-o-(2,3,4,6-tetra-o-acetylhexopyranosyl)hexopyranose

There total 8 articles about 1,2,3-Tri-o-acetyl-6-deoxy-4-o-(2,3,4,6-tetra-o-acetylhexopyranosyl)hexopyranose 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: 29.0%

1,2,3-tri-O-acetyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose (28810-03-9) → 1,2,3-tri-O-acetyl-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose (28810-04-0) + Maltose-5-en-heptaacetat (67831-15-6) + C24H32O15 (1189789-87-4) + C24H32O15 (1189789-86-3) + C52H70O34 + C52H70O34

Guidance literature:

With N,N,N,N-tetraethylammonium tetrafluoroborate; In acetonitrile; Electrolysis; Inert atmosphere;

DOI:10.1002/chem.200900825

Reference yield:

benzyl 2,3-di-O-acetyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside (84553-54-8) → 1,2,3-tri-O-acetyl-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose (28810-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / barium carbonate, hydrazin hydrate / Raney nickel / methanol

2: 1.) H₂; 2.) sodium acetate / 1.) 10percent palladium-on-carbon / 1.) acetic acid, r.t., 2 d; 2.) reflux, 15 min

With hydrogen; sodium acetate; hydrazine hydrate; barium carbonate; palladium on activated charcoal; nickel; In methanol;

DOI:10.1016/0008-6215(83)88275-5

Reference yield:

acetic anhydride (108-24-7) + benzyl 2,3-di-O-acetyl-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside (84553-55-9) → 1,2,3-tri-O-acetyl-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose (28810-04-0)

Guidance literature:

With hydrogen; sodium acetate; palladium on activated charcoal; Yield given. Multistep reaction; 1.) acetic acid, r.t., 2 d; 2.) reflux, 15 min;

DOI:10.1016/0008-6215(83)88275-5

upstream raw materials:

acetic anhydride

benzyl 2,3-di-O-acetyl-6-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside

benzyl 2,3-di-O-acetyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranoside

1,2,3-tri-O-acetyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose

Refernces

• 1、 Alberti, Angelo,Macciantelli, Dante,Naggi, Annamaria,Urso, Elena,Torri, Giangiacomo,Vismara, Elena. "Electrochemical characterisation of 6-iodomaltose, 6′-iodomaltose and 6-iodomaltotriose on a silver cathode and their one-pot electrochemical dimerisation to new mixed O/C maltotetraose and maltohexaose mimics". experimental part. p. 8005 - 8014. Retrieved 2010/03/31.
• 2、 Arita,Isemura,Ikenaka,Matsushima. "Studies on the substrate specificity of Taka-amylase A. 3. Syntheses of some new derivatives of phenyl alpha-maltoside.". . p. 818 - 823. Retrieved 2007/10/07.