(Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Base Information

• Chemical Name: (Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester
• CAS No.: 182284-82-8
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 182284-82-8.mol

Synonyms:(Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Chemical Property of (Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester

There total 1 articles about (Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester 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: 73.0%

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + (2S,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxirane-2-carbaldehyde → (Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester (182284-82-8)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(96)01460-8

Reference yield: 84.0%

(Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester (182284-82-8) → (E)-(4S,5R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4-methyl-hept-2-enoic acid methyl ester (182284-83-9)

Guidance literature:

With formic acid; tributylphosphine; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In 1,4-dioxane; Ambient temperature;

DOI:10.1016/S0040-4039(96)01460-8

Reference yield:

(Z)-3-{(2R,3R)-3-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methyl-oxiranyl}-acrylic acid methyl ester (182284-82-8) → (3R,4S)-6-((1S,2R,5S)-2-Butyl-2-methylsulfanylmethoxy-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-1-(4-methoxy-benzyloxy)-4-methyl-hexan-3-ol (182284-88-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 84 percent / n-Bu₃P, HCO₂H-Et₃N / Pd₂(dba)3*CHCl₃ / dioxane / Ambient temperature

2: 100 percent / imidazole / dimethylformamide / Ambient temperature

3: 1.) OsO₄, NMO, 2.) Pb(OAc)4 / 1.) t-BuOH, acetone, H₂O, r.t., 2.) toluene, r.t.

4: 94 percent / Ph₃P / CH₂Cl₂ / 0 °C

5: 1.) n-BuLi / 1.) THF, -78 deg C, to r.t., 2.) 0 deg C to r.t.

6: 97 percent / H₂ / Pd/C / ethyl acetate / Ambient temperature

7: 34 percent / PPTS / methanol / Ambient temperature

8: 80 percent / n-Bu₄NF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; lead(IV) acetate; osmium(VIII) oxide; n-butyllithium; formic acid; N-methyl-2-indolinone; tributylphosphine; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; triethylamine; triphenylphosphine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(96)01460-8

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

Downstream raw materials:

(E)-(4S,5R)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4-methyl-hept-2-enoic acid methyl ester

(S)-1-{(2R,5S,7R,8S)-2-Butyl-7-[2-(4-methoxy-benzyloxy)-ethyl]-8-methyl-1,6-dioxa-spiro[4.5]dec-2-yl}-ethane-1,2-diol

(3R,4S)-6-((1S,2R,5S)-2-Butyl-2-methylsulfanylmethoxy-6,8-dioxa-bicyclo[3.2.1]oct-5-yl)-1-(4-methoxy-benzyloxy)-4-methyl-hexan-3-ol

(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-pentanal