3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester

Base Information

• Chemical Name: 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester
• CAS No.: 919608-38-1
• Molecular Formula: C₃₁H₄₂O₈S
• Molecular Weight: 574.736
• Mol file: 919608-38-1.mol

Synonyms:3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester

Chemical Property of 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester

There total 18 articles about 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-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: 89.0%

toluene-4-sulfonic acid 5-benzyloxy-3-hydroxy-6-(5-methyl-tetrahydro-furan-2-yl)-heptyl ester (919608-37-0) + methyl 3,3-dimethoxy-2-methylpropionate (76526-43-7) → 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester (919608-38-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; for 2h; Heating;

DOI:10.1002/anie.200602860

Reference yield:

methanesulfonic acid 5-(1-methyl-2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester (919608-15-4) → 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester (919608-38-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

1.2: 95 percent / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 66 percent / lithium aluminum hydride / diethyl ether / 0 - 20 °C

3.1: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 97 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

5.1: 97 percent / magnesium bromide etherate / CH₂Cl₂ / 1 h / 20 °C

6.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

6.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

7.1: 851 mg / sodium borohydride / methanol / 0 - 20 °C

8.1: 92 percent / TEA / CH₂Cl₂ / 14 h / 0 °C

9.1: 89 percent / PPTS / benzene / 2 h / Heating

With sodium tetrahydroborate; lithium aluminium tetrahydride; TEA; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; magnesium bromide ethyl etherate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tet.2007.07.005

Reference yield:

{5-[2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-furan-2-yl}-methanol (919608-13-2) → 3-{3-benzyloxy-4-(5-methyl-tetrahydro-furan-2-yl)-1-[2-(toluene-4-sulfonyloxy)-ethyl]-pentyloxy}-2-methyl-acrylic acid methyl ester (919608-38-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 98 percent / TEA / CH₂Cl₂ / 0 - 20 °C

2.1: 95 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

3.1: 82 percent / PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 20 °C

4.1: TiCl₄ / CH₂Cl₂ / 0.25 h / -78 °C

4.2: 95 percent / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 66 percent / lithium aluminum hydride / diethyl ether / 0 - 20 °C

6.1: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0 - 20 °C

7.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

7.2: 97 percent / triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

8.1: 97 percent / magnesium bromide etherate / CH₂Cl₂ / 1 h / 20 °C

9.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

9.2: triphenylphosphine / CH₂Cl₂ / -78 - 20 °C

10.1: 851 mg / sodium borohydride / methanol / 0 - 20 °C

11.1: 92 percent / TEA / CH₂Cl₂ / 14 h / 0 °C

12.1: 89 percent / PPTS / benzene / 2 h / Heating

With sodium tetrahydroborate; lithium aluminium tetrahydride; 4 A molecular sieve; TEA; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; titanium tetrachloride; ozone; magnesium bromide ethyl etherate; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tet.2007.07.005

upstream raw materials:

toluene-4-sulfonic acid 5-benzyloxy-3-hydroxy-6-(5-methyl-tetrahydro-furan-2-yl)-heptyl ester

methyl 3,3-dimethoxy-2-methylpropionate

methanesulfonic acid 5-(1-methyl-2-oxo-ethyl)-tetrahydro-furan-2-ylmethyl ester

2-(5-methyl-tetrahydro-furan-2-yl)-hex-5-en-3-ol

Downstream raw materials:

C₂₄H₃₆O₄

C₂₉H₄₀O₅S

C₂₃H₃₄O₄