6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucose

Base Information

• Chemical Name: 6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucose
• CAS No.: 26184-96-3
• Molecular Formula: C₁₂H₂₂O₁₀
• Molecular Weight: 326.301
• Mol file: 26184-96-3.mol

Synonyms:EINECS 247-510-1;6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucose;SCHEMBL1877461

Chemical Property of 6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucose

Chemical Property:

• Boiling Point: 598°Cat760mmHg
• PKA: 12.10±0.70(Predicted)
• Flash Point: 315.5°C
• PSA: 169.30000
• Density: 1.66g/cm³
• LogP: -4.36960
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 326.12129689
• Heavy Atom Count: 22
• Complexity: 368

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)COC2C(C(C(C(O2)O)O)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)CO[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)O)O)O)O)O)O
• Uses: β-Rutinose is an intermediate used in the synthesis of Isorhoifolin (Diosmin EP Impurity C) (I819700), which is a naturally occurring flavonoid that was shown to exhibit potential antidiabetic, antihyperlipidemic and antioxidant effects. Also, it is an extract from the medicinal plant, Viola tricolor, for the potential treatment of acne.

Technology Process of 6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucose

There total 37 articles about 6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucose 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: 87.0%

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) + 1,2:3,4-di-O-isopropylidene-6-O-trityl-α-D-galactopyranose (76951-66-1) → 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) + 1,2:3,4-di-O-isopropylidene-6-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-galactopyranose (62043-20-3,75795-30-1)

Guidance literature:

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

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

Reference yield: 63.0%

rutin (153-18-4) → 6-O-α-L-rhamnopyranosyl-β-D-glucopyranose (552-74-9,26184-96-3,47235-47-2,56906-86-6,56942-81-5,68398-81-2,68567-48-6,68567-49-7,75828-90-9,59246-67-2) + quercetol (117-39-5,74893-81-5)

Guidance literature:

With α-L-rhamnosyl-β-D-glucosidase from Aspergillus niger K2 in Pichia pastoris; In aq. phosphate buffer; dimethyl sulfoxide; at 35 - 100 ℃; for 24h; pH=5; Enzymatic reaction;

DOI:10.1002/adsc.201400566

Reference yield: 24.0%

p-hydroxyphenethyl alcohol (501-94-0) + rutin (153-18-4) → 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) + quercetol (117-39-5,74893-81-5) + 2-(4-hydroxyphenyl)ethyl β-rutinoside

Guidance literature:

p-hydroxyphenethyl alcohol; rutin; In methanol; at 40 ℃; for 30h;

With water; In methanol; for 0.166667h; regioselective reaction; Reflux;

DOI:10.1016/j.foodchem.2020.127674

upstream raw materials:

2,3,4-tri-O-acetyl-1-O-geranyloxycarbonyl-6-O-(2,3,4-tri-O-acetyl-6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranose

5-hydroxyheptaacetyldiosmin

kaempferol-3-rutinoside

rutin

Downstream raw materials:

L-Rhamnose

D-glucose

Neryl 2,3,4-tri-O-acetyl-6-O-(2,3,4-tri-O-acetyl-6-O-deoxy-α-L-mannopyranosyl)-β-D-glucopyranoside