2-[2-[3,5-Dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Base Information

• Chemical Name: 2-[2-[3,5-Dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• CAS No.: 20318-30-3
• Molecular Formula: C₄₅H₇₃NO₁₆
• Molecular Weight: 884.072
• Mol file: 20318-30-3.mol

Synonyms:2-[2-[3,5-Dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol;a-Solamarine;AKOS037514915

Chemical Property of 2-[2-[3,5-Dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

Chemical Property:

• Melting Point: 278-281℃ (dec.) (methanol acetone )
• PKA: 12.78±0.70(Predicted)
• PSA: 258.71000
• Density: 1.42±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 0.11590
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 8
• Exact Mass: 883.49293524
• Heavy Atom Count: 62
• Complexity: 1630

Purity/Quality:

≥98% ^*data from raw suppliers

Solamargine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CC=C6C5(CCC(C6)OC7C(C(C(C(O7)CO)O)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)C)O)O)O)O)C)C)C)NC1
• Description: First isolated from Solanum marginatum, this alkaloid has also been obtained from the ripe berries of S. khasianum var. chatterjeerum sengupta. It is laevorotatory with [α]20D - 105° (c 0.986, MeOH) and forms a picrate as yellow crystals, m.p. 188-9°C; picrolonate, m.p. 204-SoC and the benzoate with an indefinite melting point. Hydrolysis with 2N methanolic HCl furnishes solasodine, m.p. 197-8°C, one mole of D-glucose and two moles of L-rhamnose.
• Uses: Solamargine is a natural steroidal glycoalkaloid produces a mild secondary effect through cortocoids produced in the adrenal glands.

Technology Process of 2-[2-[3,5-Dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol

There total 2 articles about 2-[2-[3,5-Dihydroxy-2-(hydroxymethyl)-6-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-ene-6,2'-piperidine]-16-yl)oxyoxan-4-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-methyloxane-3,4,5-triol 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: 45.0%

C86H105NO25 → solasonine (19121-58-5,20318-30-3,28701-66-8,77-34-9)

Guidance literature:

With water; sodium hydroxide; In methanol; dichloromethane; at 70 ℃; for 10h; pH=12;

Reference yield:

→ solasonine (19121-58-5,20318-30-3,28701-66-8,77-34-9)

Guidance literature:

Reference yield:

solasonine (19121-58-5,20318-30-3,28701-66-8,77-34-9) → solasodine (126-17-0)

Guidance literature:

With hydrogenchloride; water; In isopropyl alcohol; at 20 ℃; Product distribution / selectivity; Heating / reflux;

Downstream raw materials:

solasodine

(25R)-22αN-spirosola-3,5-diene

solasodine-3β-acetate

Refernces