Silychristin B

Base Information

• Chemical Name: Silychristin B
• CAS No.: 879325-58-3
• Molecular Formula: C₂₅H₂₂O₁₀
• Molecular Weight: 482.444
• ChEMBL ID: CHEMBL589325
• DSSTox Substance ID: DTXSID80858723
• Metabolomics Workbench ID: 143139,200666
• Nikkaji Number: J2.220.517J
• Wikidata: Q81977807
• Mol file: 879325-58-3.mol

Synonyms:Silychristin B;879325-58-3;(-)-Silychristin;CHEMBL589325;(2R,3R)-3,5,7-trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1-benzofuran-5-yl]-2,3-dihydrochromen-4-one;(-)-Silychristin B;SCHEMBL20152103;DTXSID80858723;HY-N8873;BDBM50526627;AKOS040762350;FS-8268;CS-0149281

Chemical Property of Silychristin B

Chemical Property:

• Boiling Point: 782.0±60.0 °C(Predicted)
• Density: 1.578±0.06 g/cm3(Predicted)
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 482.12129689
• Heavy Atom Count: 35
• Complexity: 765

Purity/Quality:

≥98% ^*data from raw suppliers

SilychristinB ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C2C(C3=C(O2)C(=CC(=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O
• Isomeric SMILES: COC1=C(C=CC(=C1)[C@@H]2[C@H](C3=C(O2)C(=CC(=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)O)CO)O

Technology Process of Silychristin B

There total 36 articles about Silychristin B 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: 19.0%

{3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone (119384-71-3,124815-78-7) → (+/-)-silychristin (33889-69-9,119435-01-7,125762-44-9,879325-58-3) + (2R,3R)-3,5,7-Trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzofuran-5-yl]-chroman-4-one (33889-69-9,119435-01-7,125762-44-9,879325-58-3)

Guidance literature:

With hydrogenchloride; In methanol; at 70 ℃; for 0.25h;

DOI:10.1248/cpb.37.1441

Reference yield: 19.0%

{3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone (119384-71-3,124815-78-7) → (+/-)-silychristin (33889-69-9,119435-01-7,125762-44-9,879325-58-3) + (2R,3R)-3,5,7-Trihydroxy-2-[(2S,3R)-7-hydroxy-2-(4-hydroxy-3-methoxy-phenyl)-3-hydroxymethyl-2,3-dihydro-benzofuran-5-yl]-chroman-4-one (33889-69-9,119435-01-7,125762-44-9,879325-58-3)

Guidance literature:

With hydrogenchloride; In methanol; at 70 ℃; for 0.25h;

DOI:10.1248/cpb.37.1441

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → (+/-)-silychristin (33889-69-9,119435-01-7,125762-44-9,879325-58-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 93 percent / KOH / ethanol

2: 87 percent / conc. HCl / methanol; dioxane

3: 92 percent / 30percent H₂O₂, 5percent NaOH / methanol; dioxane

4: 1.) BF₃*Et₂O, 2.) NaBH₄ / 1.) benzene, 0 deg C, 2.) THF

5: 66 percent / H₂ / 10percent Pd-C / methanol

6: BF₃-Et₂O / 5 °C

7: 66 percent / (i-Pr)2NEt / CH₂Cl₂

8: 91 percent / 1M NaOH / methanol

9: 95 percent / MnO₂ / CH₂Cl₂

10: 94 percent / NaOH / ethanol

11: 96 percent / 30percent H₂O₂, 5percent NaOH / methanol

12: 19 percent / conc. HCl / methanol / 70 °C

With hydrogenchloride; manganese(IV) oxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In 1,4-dioxane; methanol; ethanol; dichloromethane;

DOI:10.1039/c39880000749

upstream raw materials:

{3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-oxiranyl}-(2,4,6-tris-methoxymethoxy-phenyl)-methanone

4-benzyloxy-3-methoxyacetophenone

erythro-1-(4-hydroxy-3-methoxyphenyl)-2-(2,3-dihydroxy-5-hydroxymethylphenyl)-1,3-propanediol

3-hydroxymethyl-2-(4-hydroxy-3-methoxyphenyl)-7-hydroxy-5-acetoxymethyl-2,3-dihydrobenzofuran