(2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal

Base Information

• Chemical Name: (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal
• CAS No.: 24822-33-1
• Molecular Formula: C₁₂H₂₂O₁₁
• Molecular Weight: 342.3
• UNII: 67I334IX2M
• DSSTox Substance ID: DTXSID701015178
• Nikkaji Number: J150.529G
• Wikidata: Q76306492
• Mol file: 24822-33-1.mol

Synonyms:Isomaltose

Chemical Property of (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal

Chemical Property:

• XLogP3: -5
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 8
• Exact Mass: 342.11621151
• Heavy Atom Count: 23
• Complexity: 367

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OCC(C(C(C(C=O)O)O)O)O)O)O)O)O
• Isomeric SMILES: C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC[C@H]([C@H]([C@@H]([C@H](C=O)O)O)O)O)O)O)O)O

Technology Process of (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal

There total 18 articles about (2R,3S,4R,5R)-2,3,4,5-Tetrahydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexanal 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:

→ D-Glucose (2280-44-6) + D-isomaltose (24822-33-1) + 1,6-Anhydro-β-D-glucohexofuranose (7425-74-3) + levoglucosan (498-07-7)

Guidance literature:

With sulfuric acid; In water; at 250 ℃; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/0008-6215(89)80040-0

Reference yield:

Isomaltulose (497-84-7,15132-06-6,58166-27-1,13718-94-0) → D-Fructose (57-48-7,18875-34-8) + D-isomaltose (24822-33-1) + D-Mannose (3458-28-4) + D-glucose (50-99-7)

Guidance literature:

With water; In ethanol; at 200 ℃; under 75007.5 Torr; Solvent; Kinetics; Supercritical conditions;

DOI:10.1080/09168451.2015.1127135

Reference yield:

levodopa (59-92-7,90638-38-3) + Sucrose (57-50-1) → D-Fructose (57-48-7,18875-34-8) + D-isomaltose (24822-33-1) + Isomaltulose (497-84-7,15132-06-6,58166-27-1,13718-94-0) + α-D-Glcp-(1->6)-α-D-Glcp-(1->6)-α-D-Glcp-(1->6)-D-Glcp (15785-89-4) + leucrose (5-O-α-D-glucopyranosyl-β-D-fructopyranose) (470-16-6,58166-26-0,100430-38-4,130853-03-1,7158-70-5) + isomaltotriose (455-50-5) + D-glucose (50-99-7) + 4-O-α-D-glucopyranosyl L-DOPA (155611-80-6) + 3-O-α-D-glucopyranosyl L-DOPA (155611-79-3)

Guidance literature:

With glucansucrases from Leuconostoc mesenteroides; In pyridinium acetate buffer; at 23 ℃; for 24h; pH=5.2; Enzymatic reaction;

DOI:10.1016/j.carres.2010.05.001

upstream raw materials:

6²-β-D-glucopyranosyl-laminaratriose

azukisaponin VI

p-nitrophenyl 6-O-β-D-glucopyranosyl-β-D-glucopyranoside

D-Fructose

Downstream raw materials:

formic acid

O-β-D-glucopyranosylglycolic acid

(S)-6-((2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-hexane-1,2,3,4,5-pentaol

2-O-β-D-Glucopyranosyl-D-erythronic acid

Refernces

• 1、 Hattori, Takeshi,Kato, Yasuna,Uno, Shuji,Usui, Taichi. "Mode of action of a β-(1→6)-glucanase from Penicillium multicolor". . p. 6 - 16. Retrieved 2013/02/25.
• 2、 Yoon, Seung-Heon,Fulton, D. Bruce,Robyt, John F.. "Enzymatic synthesis of l-DOPA α-glycosides by reaction with sucrose catalyzed by four different glucansucrases from four strains of Leuconostoc mesenteroides". experimental part. p. 1730 - 1735. Retrieved 2010/10/19.