(E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester

Base Information

• Chemical Name: (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester
• CAS No.: 157811-05-7
• Molecular Formula: C₂₇H₄₀O₇
• Molecular Weight: 476.61
• Mol file: 157811-05-7.mol

Synonyms:(E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester

Chemical Property of (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester

There total 11 articles about (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic 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: 99.5%

1-methoxy-2-methyl-1-<(trimethylsilyl)oxy>-1,3-butadiene (95393-81-0) + {(2R,6S)-6-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde (157811-04-6) → (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester (157811-05-7)

Guidance literature:

With boron trifluoride diethyl etherate; In diethyl ether; dichloromethane; at -78 ℃;

DOI:10.1039/c39940001147

Reference yield:

(R)-2-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-oxirane (157758-29-7) → (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester (157811-05-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) 1,3-dimethyl-3,4,5-tetrahydro-2(1H)-pyrimidinone, n-BuLi, 2.) H₂SO₄, 3.) TsOH, 4.) Et₃N, 1,8-diazabicyclo<5.4.0>undec-7-ene

2: 95 percent / diisobutylaluminium hydride / CH₂Cl₂ / 0.5 h / -78 °C

3: 65 percent / ZnCl₂ / CH₂Cl₂ / 0.25 h / -20 °C

4: 99.5 percent / BF₃*OEt₂ / CH₂Cl₂; diethyl ether / -78 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In diethyl ether; dichloromethane;

DOI:10.1039/c39940001147

Reference yield:

(2S,4S,5S)-4-Methoxy-6-(4-methoxy-benzyloxy)-5-methyl-hexane-1,2-diol → (E)-(S)-5-Hydroxy-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester (157811-05-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 14 h

2: 97 percent / Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

3: 91 percent / TBAF / tetrahydrofuran / 10 h / 25 °C

4: 1.) 1,3-dimethyl-3,4,5-tetrahydro-2(1H)-pyrimidinone, n-BuLi, 2.) H₂SO₄, 3.) TsOH, 4.) Et₃N, 1,8-diazabicyclo<5.4.0>undec-7-ene

5: 95 percent / diisobutylaluminium hydride / CH₂Cl₂ / 0.5 h / -78 °C

6: 65 percent / ZnCl₂ / CH₂Cl₂ / 0.25 h / -20 °C

7: 99.5 percent / BF₃*OEt₂ / CH₂Cl₂; diethyl ether / -78 °C

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/c39940001147

upstream raw materials:

1-methoxy-2-methyl-1-<(trimethylsilyl)oxy>-1,3-butadiene

{(2R,6S)-6-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde

(R)-2-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-oxirane

(S)-6-[(2S,3S)-2-Methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-pyran-2-one

Downstream raw materials:

(E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(2S,3S)-2-methoxy-4-(4-methoxy-benzyloxy)-3-methyl-butyl]-5,6-dihydro-2H-pyran-2-yl}-2-methyl-hex-2-enoic acid methyl ester