4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal

Base Information

• Chemical Name: 4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal
• CAS No.: 1109-28-0
• Molecular Formula: C₁₈H₃₂O₁₆
• Molecular Weight: 504.442
• Hs Code.: 29400090
• NSC Number: 170180
• Mol file: 1109-28-0.mol

Synonyms:NSC-170180;NSC170180;4-[3,4-dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal;FABC4C0B-2B58-432A-8E16-A4967FA902B6

Chemical Property of 4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 6.5E-35mmHg at 25°C
• Melting Point: 132-135 °C
• Refractive Index: 1.673
• Boiling Point: 958.9 °C at 760 mmHg
• PKA: 12.39±0.20(Predicted)
• Flash Point: 329.7 °C
• PSA: 268.68000
• Density: 1.75 g/cm³
• LogP: -7.57300
• Storage Temp.: +15C to +30C
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: Soluble in water.
• XLogP3: -7.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 11
• Exact Mass: 504.16903493
• Heavy Atom Count: 34
• Complexity: 625

Purity/Quality:

99% ^*data from raw suppliers

D-Maltotriose ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC(C(CO)O)C(C(C=O)O)O)CO)O)O)O)O
• Uses: A trisaccharide resulting from the digestion of Amalose by α-Amalase. displays potent and selective in vitro anti-human immunodeficiency virus type 1 activity. Prepared by modification of lysine e-amino groups Maltotriose is a matrose regulon inducer in Escherichia coli. Maltotriose has been used in a study to investigate the influence of fourth generation poly(propyleneimine) dendrimers on blood cells.

Technology Process of 4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal

There total 37 articles about 4-[3,4-Dihydroxy-6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal 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: 74.0%

benzyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1<*>4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside → maltotriose (6401-81-6,17659-52-8,19141-16-3,20702-55-0,52485-13-9,69429-19-2,80446-86-2,80446-87-3,94799-30-1,94799-74-3,113158-51-3,118396-93-3,121153-20-6,133267-59-1,1109-28-0,142185-35-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In acetic acid; at 25 ℃;

DOI:10.1246/bcsj.65.3257

Reference yield:

2-chloro-4-nitrophenol-α-D-maltotrioside (118291-90-0,157381-11-8,165522-16-7) → maltotriose (6401-81-6,17659-52-8,19141-16-3,20702-55-0,52485-13-9,69429-19-2,80446-86-2,80446-87-3,94799-30-1,94799-74-3,113158-51-3,118396-93-3,121153-20-6,133267-59-1,1109-28-0,142185-35-1) + 2-chloro-4-nitrophenol (619-08-9) + 4-nitrophenyl α-maltotrioside (66451-58-9) + 2-chloro-4-nitrophenyl α-D-glucopyranoside (119047-14-2) + C30H44ClNO23 + C42H64ClNO33

Guidance literature:

With human salivary alpha-amylase; MES-buffer; sodium chloride; calcium chloride; In water; at 37 ℃; for 0.166667h; Product distribution; Mechanism; Km and V_max determination, effect of KSCN and maltopenaose, concentration dependence;

DOI:10.1016/S0008-6215(97)00150-X

Reference yield:

2,4-dinitrophenyl α-maltotrioside (754201-87-1) → 2,4-Dinitrophenol (51-28-5) + maltotriose (6401-81-6,17659-52-8,19141-16-3,20702-55-0,52485-13-9,69429-19-2,80446-86-2,80446-87-3,94799-30-1,94799-74-3,113158-51-3,118396-93-3,121153-20-6,133267-59-1,1109-28-0,142185-35-1) + 2-(6-{6-[6-(2,4-dinitro-phenoxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy}-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:

With human pancreatic α-amylase; In phosphate buffer; at 30 ℃; for 0.333333h; pH=6.9; Kinetics; Enzymatic reaction;

DOI:10.1016/j.carres.2004.05.019

upstream raw materials:

Sucrose

D-maltose

β‐cyclodextrin

D-maltohexaose

Downstream raw materials:

D-glucose

C₄₅H₆₃NO₁₉S

C₄₄H₆₅N₅O₂₀

maltotriose peracetate

Refernces

α-Glucosidases inhibitors. II

10.1002/jlac.198319831106

The research focuses on the synthesis of modified maltooligosaccharides, specifically targeting the 4"-amino-4",6"-dideoxymaltooligosaccharide derivative 5, which is the O-protected terminal trisaccharide unit of acarbose—an α-glucosidase inhibitor used in the treatment of metabolic disorders. The study developed two independent pathways for the synthesis of the benzyl-protected trisaccharide block 5. The first method involved glycosidic linkage between activated viosamine derivatives and 4'-unprotected maltose, while the second method focused on the direct transformation of the 4",6"-hydroxyl groups of maltotriose. Key chemicals used in the synthesis process include 4-azido-4,6-dideoxyglucose, trichloroacetimidate, phenylmaltotrioside, and various protecting groups such as benzyl and acetyl groups. The conclusions of the research detailed the successful synthesis of the desired trisaccharide units and their derivatives, which could potentially contribute to the development of more effective α-glucosidase inhibitors.