9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester
• CAS No.: 104322-84-1
• Molecular Formula: C₄₉H₆₆O₉
• Molecular Weight: 799.058
• Mol file: 104322-84-1.mol

Synonyms:

Chemical Property of 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester

There total 16 articles about 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic 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:

benzyl bromide (100-39-0) → 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester (104322-84-1)

Guidance literature:

Multi-step reaction with 16 steps

2: 87 percent / ClCOCOCl, Me₂SO / CH₂Cl₂ / -78 °C

3: 79 percent / 9-BBN triflate, diisopropylamine / diethyl ether / -78 - 0 °C

4: 85 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 22 °C

5: 1.) TsCl, DMAP, Et₃N, 2.) TsOH, NaOCH₃ / 1.) CH₂Cl₂, 22 deg C, 4 h, 2.) MeOH, 22 deg C, 16 h

6: Et₃N, DMAP / CH₂Cl₂

7: NaH / tetrahydrofuran / 12 h

8: O₃, pyridine / CH₂Cl₂

10: 76 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂

11: 1.) CeI₃ / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF

12: 75 percent / CBr₄, BaCO₃, Ph₃P / CH₂Cl₂ / 0.75 h

13: 82 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 65 °C

14: 98 percent / PPTs / methanol / 14 h / 22 °C

15: MnO₂ / tetrahydrofuran / 5 h

16: NaCN / acetic acid / 16 h

With pyridine; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; cerium(III) triiodide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; 3 A molecular sieve; sodium cyanide; tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; triphenylphosphine; barium carbonate; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; toluene;

DOI:10.1021/jo00370a040

Reference yield:

(R)-2-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol (104322-67-0) → 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester (104322-84-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 87 percent / ClCOCOCl, Me₂SO / CH₂Cl₂ / -78 °C

2: 79 percent / 9-BBN triflate, diisopropylamine / diethyl ether / -78 - 0 °C

3: 85 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 22 °C

4: 1.) TsCl, DMAP, Et₃N, 2.) TsOH, NaOCH₃ / 1.) CH₂Cl₂, 22 deg C, 4 h, 2.) MeOH, 22 deg C, 16 h

5: Et₃N, DMAP / CH₂Cl₂

6: NaH / tetrahydrofuran / 12 h

7: O₃, pyridine / CH₂Cl₂

9: 76 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂

10: 1.) CeI₃ / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF

11: 75 percent / CBr₄, BaCO₃, Ph₃P / CH₂Cl₂ / 0.75 h

12: 82 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 65 °C

13: 98 percent / PPTs / methanol / 14 h / 22 °C

14: MnO₂ / tetrahydrofuran / 5 h

15: NaCN / acetic acid / 16 h

With pyridine; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; cerium(III) triiodide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; 3 A molecular sieve; sodium cyanide; tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; triphenylphosphine; barium carbonate; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; toluene;

DOI:10.1021/jo00370a040

Reference yield:

(2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde (104322-68-1) → 9-{(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enoyloxy}-nonanoic acid methyl ester (104322-84-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 79 percent / 9-BBN triflate, diisopropylamine / diethyl ether / -78 - 0 °C

2: 85 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 22 °C

3: 1.) TsCl, DMAP, Et₃N, 2.) TsOH, NaOCH₃ / 1.) CH₂Cl₂, 22 deg C, 4 h, 2.) MeOH, 22 deg C, 16 h

4: Et₃N, DMAP / CH₂Cl₂

5: NaH / tetrahydrofuran / 12 h

6: O₃, pyridine / CH₂Cl₂

8: 76 percent / PDC, 3 Angstroem molecular sieves / CH₂Cl₂

9: 1.) CeI₃ / 1.) THF, from -100 deg C to 0 deg C, 30 min, 2.) THF

10: 75 percent / CBr₄, BaCO₃, Ph₃P / CH₂Cl₂ / 0.75 h

11: 82 percent / n-Bu₃SnH, AIBN / toluene / 1 h / 65 °C

12: 98 percent / PPTs / methanol / 14 h / 22 °C

13: MnO₂ / tetrahydrofuran / 5 h

14: NaCN / acetic acid / 16 h

With pyridine; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; cerium(III) triiodide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; 3 A molecular sieve; sodium cyanide; tri-n-butyl-tin hydride; sodium methylate; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; triphenylphosphine; barium carbonate; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; toluene;

DOI:10.1021/jo00370a040

upstream raw materials:

methyl 9-hydroxynonanoate

(E)-4-[(2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-3-methyl-but-2-enal

benzyl bromide

(R)-2-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol

Downstream raw materials:

pseudomonic acid C