(E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

• Chemical Name: (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS No.: 137585-74-1
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397
• Mol file: 137585-74-1.mol

Synonyms:(E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property of (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 1 articles about (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl 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: 90.0%

(R)-2-Ethynyl-1-methyl-cyclohex-2-enecarboxylic acid methyl ester (137779-96-5) + 5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose (137585-73-0) → (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (137585-74-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/S0957-4166(00)82200-4

Reference yield:

n-heptylmagnesium bromide (13125-66-1) + (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (137585-74-1) → 3-Methyl-decanoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (137585-91-2,137586-18-6)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; Yield given. Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 2 h;

DOI:10.1016/S0957-4166(00)82200-4

Reference yield:

vinyl magnesium bromide (1826-67-1) + (E)-But-2-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (137585-74-1) → 3-Methyl-pent-4-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (137585-89-8,137604-54-7)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; Yield given. Multistep reaction; 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 2 h;

DOI:10.1016/S0957-4166(00)82200-4

upstream raw materials:

(R)-2-Ethynyl-1-methyl-cyclohex-2-enecarboxylic acid methyl ester

5,6-dideoxy-1,2-O-(isopropylidene)-6-phenyl-α-D-xylo-hexofuranose

Downstream raw materials:

3-Methyl-decanoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

3-Methyl-pent-4-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

3-Methyl-hex-5-enoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

3-Methyl-pentanoic acid (3aR,5R,6S,6aR)-2,2-dimethyl-5-phenethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester