(Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester

Base Information

• Chemical Name: (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester
• CAS No.: 197011-83-9
• Molecular Formula: C₂₁H₃₀O₆
• Molecular Weight: 378.466
• Mol file: 197011-83-9.mol

Synonyms:(Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester

Chemical Property of (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester

There total 14 articles about (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl 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: 10.0%

ethyl (2-dimethoxyphosphinyl)-2-propanoate (80673-78-5) + (2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-carbaldehyde → (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester (197011-83-9) + (E)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester

Guidance literature:

With sodium hydride; at -78 ℃; for 3h; Yield given;

DOI:10.1016/S0040-4039(97)01586-4

Reference yield:

(4S,5S,6S)-4,5-di-acetyloxy-6-methoxy-5,6-dihydro-4H-pyran-2-carbaldehyde (22860-20-4) → (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester (197011-83-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 85 percent / NaBH₄, IR 120(H¹⁺) resin, / methanol / 0.08 h / 0 °C

2: Et₃Zn / CH₂Cl₂ / 10 h / -20 °C

3: 92 percent / Ph₃P, CBr₄ / CH₂Cl₂ / 1 h / Ambient temperature

4: 1.) 9-BBN; 2.) NaOAc, H₂O₂; 3.) imidazole, DMAP / 1.) THF, 4 h; 2.) 0 deg C, 3 h; 3.) CH₂Cl₂, rt. 4 h

5: 93 percent / NaOMe / methanol / 0.17 h / Ambient temperature

6: 97 percent / PPTS / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 81 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

8: pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

9: Bu₃SnH, AIBN / toluene / 2 h / Ambient temperature

10: 89 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

11: 91 percent / (COCl)2, DMSO, Et₃N / 0.5 h / -78 °C

12: NaH / 3 h / -78 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; Et₃Zn; IR 120(H¹⁺) resin; tetrabutyl ammonium fluoride; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium methylate; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(97)01586-4

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (Z)-3-[(2S,3S,4R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-tetrahydro-pyran-2-yl]-2-methyl-acrylic acid ethyl ester (197011-83-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / PPTS / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 81 percent / DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

3: pyridine, DMAP / CH₂Cl₂ / 6 h / Ambient temperature

4: Bu₃SnH, AIBN / toluene / 2 h / Ambient temperature

5: 89 percent / Bu₄NF / tetrahydrofuran / 1 h / Ambient temperature

6: 91 percent / (COCl)2, DMSO, Et₃N / 0.5 h / -78 °C

7: NaH / 3 h / -78 °C

With pyridine; dmap; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(97)01586-4

upstream raw materials:

ethyl (2-dimethoxyphosphinyl)-2-propanoate

(4S,5S,6S)-4,5-di-acetyloxy-6-methoxy-5,6-dihydro-4H-pyran-2-carbaldehyde

p-Anisaldehyde dimethyl acetal

Acetic acid (2S,3S,4S)-4-acetoxy-6-hydroxymethyl-2-methoxy-3,4-dihydro-2H-pyran-3-yl ester