Phenethyl rutinoside

Base Information

• Chemical Name: Phenethyl rutinoside
• CAS No.: 88510-08-1
• Molecular Formula: C₂₀H₃₀O₁₀
• Molecular Weight: 430.452
• Wikidata: Q105193771
• Mol file: 88510-08-1.mol

Synonyms:Phenethyl rutinoside;2-methyl-6-[[3,4,5-trihydroxy-6-(2-phenylethoxy)oxan-2-yl]methoxy]oxane-3,4,5-triol;88510-08-1;CHEBI:167920;1,2-Hexadecanediol (8CI)(9CI)

Chemical Property of Phenethyl rutinoside

Chemical Property:

• XLogP3: -1.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 430.18389715
• Heavy Atom Count: 30
• Complexity: 516

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OCCC3=CC=CC=C3)O)O)O)O)O)O

Technology Process of Phenethyl rutinoside

There total 12 articles about Phenethyl rutinoside 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: 98.0%

phenylethyl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside (88510-13-8) → 2-phenylethyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (88510-08-1)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/0008-6215(90)80004-M

Reference yield:

2-phenylethanol (60-12-8) → 2-phenylethyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (88510-08-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 34 percent / immobilized β-D-glucosidase (EC 3.2.1.21) / H2O / 96 h / 50 °C

2: 65 percent / pyridine / 24 h / 20 °C

3: 99 percent / 4-N,N-dimethylaminopyridine (DMAP) / pyridine / 1 h / 20 °C

4: 97 percent / H₂ / Pd(OH)2-C / methanol

5: 81 percent / phenylselenochloride (PhSeCl); silver triflate (AgOTf); 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 1 h / 0 °C

6: 85 percent / K₂CO₃ / methanol / 0.5 h / 20 °C

With dmap; Phenylselenyl chloride; 4 A molecular sieve; immobilized β-D-glucosidase (EC 3.2.1.21); hydrogen; silver trifluoromethanesulfonate; potassium carbonate; palladium hydroxide - carbon; In pyridine; methanol; water; 1,2-dichloro-ethane;

DOI:10.3987/COM-05-10383

Reference yield:

2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranosyl trichloracetamide (127243-74-7) → 2-phenylethyl O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (88510-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / boron trifluoride etherate / benzene; CH₂Cl₂ / 2 h / Ambient temperature

2: 98 percent / sodium methoxide / methanol / Ambient temperature

With sodium methylate; boron trifluoride diethyl etherate; In methanol; dichloromethane; benzene;

DOI:10.1016/0008-6215(90)80004-M

upstream raw materials:

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

phenethyl 2,3,4-tri-O-acetyl-β-D-glucopyranoside

phenethyl 6-O-trityl-β-D-glucopyranoside

phenethyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside

Downstream raw materials:

rutinose

2-phenylethanol

Refernces

• 1、 Voirin, Stephane,Baumes, Raymond,Bayonove, Claude,M'Bairaroua, Oubadjim,Tapiero, Claude. "Synthesis and n.m.r. spectral properties of grape monoterpenyl glycosides". . p. 39 - 56. Retrieved 2007/10/02.