{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

Base Information

• Chemical Name: {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
• CAS No.: 119384-71-3
• Molecular Formula: C₃₇H₄₆O₁₆
• Molecular Weight: 746.763
• Mol file: 119384-71-3.mol

Synonyms:

Chemical Property of {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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of {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

There total 17 articles about {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 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: 96.0%

(E)-3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-1-(2,4,6-tris-methoxymethoxy-phenyl)-propenone (119384-70-2) → {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)

Guidance literature:

With sodium hydroxide; dihydrogen peroxide; In methanol; for 4h; Ambient temperature;

DOI:10.1248/cpb.37.1441

Reference yield:

4-benzyloxy-3-methoxyacetophenone (1835-11-6) → {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)

Guidance literature:

Multi-step reaction with 11 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

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

Reference yield:

1-(4-benzyloxy-3-methoxyphenyl)-3-(2,3-dibenzyloxy-5-formylphenyl)-2-propen-1-one (124662-51-7) → {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)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / 30percent H₂O₂, 5percent NaOH / methanol; dioxane

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

3: 66 percent / H₂ / 10percent Pd-C / methanol

4: BF₃-Et₂O / 5 °C

5: 66 percent / (i-Pr)2NEt / CH₂Cl₂

6: 91 percent / 1M NaOH / methanol

7: 95 percent / MnO₂ / CH₂Cl₂

8: 94 percent / NaOH / ethanol

9: 96 percent / 30percent H₂O₂, 5percent NaOH / methanol

With manganese(IV) oxide; 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:

(E)-3-[(2S,3R)-7-Methoxymethoxy-2-(3-methoxy-4-methoxymethoxy-phenyl)-3-methoxymethoxymethyl-2,3-dihydro-benzofuran-5-yl]-1-(2,4,6-tris-methoxymethoxy-phenyl)-propenone

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

Downstream raw materials:

(+/-)-silychristin

(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