allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 213406-86-1
• Molecular Formula: C₃₀H₃₈O₁₄
• Molecular Weight: 622.623
• Mol file: 213406-86-1.mol

Synonyms:allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property of allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside

There total 2 articles about allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside 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: 80.4%

2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide (69980-52-5) + allyl 2-O-acetyl-4,6-O-benzylidene-α-D-glucopyranoside (213406-85-0) → allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside (213406-86-1)

Guidance literature:

With mercury(II) cyanide; In toluene; for 4h; Heating;

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

Reference yield:

1-O-allyl-4,6-O-benzylidene-α-D-glucopyranoside (65987-12-4) → allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside (213406-86-1)

Guidance literature:

Multi-step reaction with 2 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

With mercury(II) cyanide; sodium hydride; mercury dichloride; In toluene;

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

Reference yield:

allyl 2-O-acetyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-4,6-O-benzylidene-α-D-glucopyranoside (213406-86-1) → (E)-3-(4-Hydroxy-phenyl)-acrylic acid (2R,3R,4S,5R,6R)-5-acetoxy-3-hydroxy-6-[2-(4-hydroxy-phenyl)-ethoxy]-4-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 7 steps

1: 78.1 percent / p-TsOH / methanol; H₂O / 2 h / Heating

2: 89.9 percent / tetrahydrofuran; pyridine / 6 h / Ambient temperature

3: 93.5 percent / PdCl₂, CuCl, H₂O / tetrahydrofuran / 2 h / 25 - 30 °C

4: CHCl₃ / 5 h / Heating

5: 2,6-di-tert-butyl-4-methylpyridine, Me₃SiOTf / CH₂Cl₂ / 48 h / -15 deg C to r.t.

6: PdCl₂, CuCl, H₂O / tetrahydrofuran / 6 h / 25 - 30 °C

7: NH₄OH / methanol / 5 h / 5 - 10 °C

With ammonium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; water; toluene-4-sulfonic acid; copper(l) chloride; palladium dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water;

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

upstream raw materials:

2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide

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

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

Downstream raw materials:

(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

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