(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

Base Information

Chemical Name:(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
CAS No.:104322-83-0
Molecular Formula:C₃₉H₄₈O₆
Molecular Weight:612.807
Hs Code.:

Synonyms:

Suppliers and Price of (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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (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

There total 15 articles about (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 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:

: 100-39-0
benzyl bromide

: 104322-83-0
(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

Guidance literature:: Multi-step reaction with 15 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

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; 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; toluene;
DOI:10.1021/jo00370a040

Reference yield:

: 104322-82-9
(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-en-1-ol

: 104322-83-0
(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

Guidance literature:: With manganese(IV) oxide; In tetrahydrofuran; for 5h;
DOI:10.1021/jo00370a040

Reference yield:

: 104322-68-1
(2S)-benzyloxy-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

: 104322-83-0
(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

Guidance literature:: Multi-step reaction with 13 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

With pyridine; dmap; manganese(IV) oxide; lithium aluminium tetrahydride; dipyridinium dichromate; cerium(III) triiodide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; 3 A molecular sieve; 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; toluene;
DOI:10.1021/jo00370a040