b-D-Maltose octaacetate

Base Information

• Chemical Name: b-D-Maltose octaacetate
• CAS No.: 22352-19-8
• Molecular Formula: C28H38O19
• Molecular Weight: 678.598
• Hs Code.: 2940000080
• European Community (EC) Number: 606-994-8
• Nikkaji Number: J119.582D
• Mol file: 22352-19-8.mol

Synonyms:b-D-Maltose octaacetate;22352-19-8;octaacetyl-beta-maltose;Beta-D-maltose octaacetate;(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-(((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2,3,4-triyl triacetate;[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate;Octaacetyl beta-maltose;Maybridge1_004338;SCHEMBL424516;HMS553N06;AKOS016009417;AS-39886;CS-0171659;(2S,3R,4S,5R,6R)-6-(acetoxymethyl)-5-(((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2,3,4-triyltriacetate

Chemical Property of b-D-Maltose octaacetate

Chemical Property:

• Vapor Pressure: 1.64E-18mmHg at 25°C
• Melting Point: 159-160 °C
• Refractive Index: 1.507
• Boiling Point: 683.055 °C at 760 mmHg
• Flash Point: 281.178 °C
• PSA: 293.09000
• Density: 1.37 g/cm³
• LogP: -3.88880
• Storage Temp.: −20°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 20
• Exact Mass: 678.20072898
• Heavy Atom Count: 47
• Complexity: 1200

Purity/Quality:

99%, ^*data from raw suppliers

b-D-Maltose octaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(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
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)C)OC(=O)C)OC(=O)C)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Octaacetyl-β-maltose is used to prepare self-reproducing micelles in the preparation of triazole-containing disaccharides. It has also been used as a reactant in the synthesis of neoglycoconjugates through glycosyl aldehydes featuring bioorthogonal oxime bond formation.

Technology Process of b-D-Maltose octaacetate

There total 2 articles about b-D-Maltose octaacetate 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: 28.0%

1,2,3,6-tetra-O-acetyl-4-O-trityl-β-D-glucopyranose (99337-73-2) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate (127066-70-0) → trityl isothiocyanate (1726-94-9) + β-cellobioseoctaacetate (20764-63-0) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate (22352-19-8)

Guidance literature:

triphenylmethyl perchlorate; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80593-1

Reference yield:

acetic anhydride (108-24-7) + syringic aldehyde (134-96-3) + 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0) → 4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3) + 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) + 3,5-Dimethoxy-4-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>benzaldehyde (141243-30-3)

Guidance literature:

With pyridine; sodium hydroxide; Yield given. Multistep reaction; 1) acetone, r.t., 2) 90 deg C, 50 min.;

DOI:10.1016/S0008-6215(00)90495-6

Reference yield:

Acetyl bromide (506-96-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl acetate (22352-19-8) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Guidance literature:

DOI:10.1021/ja01111a019

upstream raw materials:

1,2,3,6-tetra-O-acetyl-4-O-trityl-β-D-glucopyranose

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate

acetic anhydride

syringic aldehyde

Downstream raw materials:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tetra-O-acetyl-β-D-glucopyranoside

phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside

phenyl-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside]

O²,O³,O⁶-Triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-D-glucose

Refernces

• 1、 Kochetkov, Nikolay K.,Klimov, Evgeny M.,Malysheva, Nelly N.. "NOVEL HIGHLY STEREOSPECIFIC METHOD OF 1,2-CIS-GLYCOSYLATION. SYNTHESIS OF α-D-GLUCOSYL-D-GLUCOSES". . p. 5459 - 5462. Retrieved 2007/10/02.