(E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 213406-88-3
• Molecular Formula: C₃₄H₄₂O₁₇
• Molecular Weight: 722.697
• Mol file: 213406-88-3.mol

Synonyms:(E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 4 articles about (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl 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: 89.9%

p-acetoxycinnamoyl chloride (53901-95-4,108608-06-6,58523-18-5) + allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (213406-87-2) → (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (213406-88-3)

Guidance literature:

In tetrahydrofuran; pyridine; for 6h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00092-5

Reference yield:

1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside (65987-12-4) → (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (213406-88-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH; 2.) HgCl₂ / 1.) THF, r.t., 20 min; 2.) THF, r.t., 20 min; 3.) THF, 0 deg C, 2 h

2: 80.4 percent / Hg(CN)2 / toluene / 4 h / Heating

3: 78.1 percent / p-TsOH / methanol; H₂O / 2 h / Heating

4: 89.9 percent / tetrahydrofuran; pyridine / 6 h / Ambient temperature

With mercury(II) cyanide; sodium hydride; toluene-4-sulfonic acid; mercury dichloride; In tetrahydrofuran; pyridine; methanol; water; toluene;

DOI:10.1016/S0008-6215(98)00092-5

Reference yield:

allyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (213406-85-0) → (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-5-acetoxy-6-allyloxy-3-hydroxy-4-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (213406-88-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 80.4 percent / Hg(CN)2 / toluene / 4 h / Heating

2: 78.1 percent / p-TsOH / methanol; H₂O / 2 h / Heating

3: 89.9 percent / tetrahydrofuran; pyridine / 6 h / Ambient temperature

With mercury(II) cyanide; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; water; toluene;

DOI:10.1016/S0008-6215(98)00092-5

upstream raw materials:

p-acetoxycinnamoyl chloride

allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside

allyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside