Rutinose heptaacetylrutinose

Base Information

• Chemical Name: Rutinose heptaacetylrutinose
• CAS No.: 5239-09-8
• Molecular Formula: C₂₆H₃₆O₁₇
• Molecular Weight: 620.562
• European Community (EC) Number: 226-037-4
• UNII: 2OBJ2V67OI
• DSSTox Substance ID: DTXSID90966803
• Nikkaji Number: J297.953E
• Wikidata: Q82949224
• Mol file: 5239-09-8.mol

Synonyms:Rutinose heptaacetylrutinose;5239-09-8;2OBJ2V67OI;[(2S,3S,4R,5R,6R)-4,5-diacetyloxy-2-methyl-6-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-3-yl] acetate;EINECS 226-037-4;UNII-2OBJ2V67OI;RUTINOSE, HEPTAACETATE;.BETA.-HEPTAACETYLRUTINOSE;DTXSID90966803;RUTINOSE HEPTAACETYLRUTINOSE [MI];RUTINOSE, HEPTAACETATE, .BETA.-;1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-deoxyhexopyranosyl)hexopyranose;6-O-(2,3,4-Tri-O-acetyl-6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucose tetraacetate;.BETA.-D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 1,2,3,4-TETRAACETATE;.BETA.-D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, TETRAACETATE;D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, 1,2,3,4-TETRAACETATE;D-GLUCOPYRANOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, TETRAACETATE;D-GLUCOSE, 6-O-(2,3,4-TRI-O-ACETYL-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-, TETRAACETATE

Chemical Property of Rutinose heptaacetylrutinose

Chemical Property:

• PSA: 211.79000
• LogP: -0.37400
• XLogP3: -0.2
• 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

β-Heptaacetylrutinose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: β-Heptaacetylrutinose is an intermediate in synthesizing Isorhoifolin (I819700), a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects.

Technology Process of Rutinose heptaacetylrutinose

There total 7 articles about Rutinose heptaacetylrutinose 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: 97.0%

rutinose (26184-96-3,552-74-9,47235-47-2,56906-86-6,56942-81-5,59246-67-2,68398-81-2,68567-48-6,68567-49-7,75828-90-9) + acetic anhydride (108-24-7) → Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside (5239-09-8,17073-40-4,29202-64-0,59684-89-8,62075-51-8,68398-82-3,70613-83-1,75828-89-6)

Guidance literature:

In pyridine; at 20 ℃;

Reference yield: 85.0%

1,2,3,4-tetra-O-acetyl-6-O-trityl-β-D-glucopyranose (37074-90-1) + Acetic acid (3aR,5S,6S,7R,7aR)-6-acetoxy-2-ethylsulfanyl-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester (75512-98-0) → Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside (5239-09-8,17073-40-4,29202-64-0,59684-89-8,62075-51-8,68398-82-3,70613-83-1,75828-89-6)

Guidance literature:

With 2,4,6-trimethyl-pyridine; triphenylmethyl perchlorate; In dichloromethane;

DOI:10.1016/S0008-6215(00)84672-8

Reference yield:

rutin (153-18-4) → Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside (5239-09-8,17073-40-4,29202-64-0,59684-89-8,62075-51-8,68398-82-3,70613-83-1,75828-89-6)

Guidance literature:

With acetic acid; Multistep reaction; 1.) reflux, 2 h; 2.) H₂O;

DOI:10.1016/0031-9422(82)83034-3

upstream raw materials:

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

Acetic acid (3aR,5S,6S,7R,7aR)-6-acetoxy-2-ethylsulfanyl-2,5-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester

rutin

acetic anhydride

Downstream raw materials:

(R,S)-linalyl 6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside

(R,S)-α-terpinyl 6-O-(α-L-rhamnopyranosyl)-β-D-glucopyranoside

Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-2-[1-methyl-1-(4-methyl-cyclohex-3-enyl)-ethoxy]-6-((2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-3-yl ester

benzyl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside

Refernces

• 1、 Williams, Patrick J.,Strauss, Christopher R.,Wilson, Bevan,Massy-Westropp, Ralph A.. "NOVEL MONOTERPENE DISACCHARIDE GLYCOSIDES OF VITIS VINIFERA GRAPES AND WINES". . p. 2013 - 2020. Retrieved 2007/10/02.