Technology Process of (E)-1-[(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-2-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-en-1-ol
There total 11 articles about (E)-1-[(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-2-methyl-4-(tetrahydro-pyran-2-yloxy)-but-2-en-1-ol 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:
- Guidance literature:
-
Multi-step reaction with 11 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
With
pyridine; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; cerium(III) triiodide; 3 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00370a040
- Guidance literature:
-
Multi-step reaction with 10 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
With
pyridine; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; cerium(III) triiodide; 3 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00370a040
- Guidance literature:
-
Multi-step reaction with 9 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
With
pyridine; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; cerium(III) triiodide; 3 A molecular sieve; sodium methylate; sodium hydride; toluene-4-sulfonic acid; ozone; triethylamine; diisopropylamine; p-toluenesulfonyl chloride; B-(trifluoromethanesulfonyloxy)-9-borabicyclo[3.3.1]nonane;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00370a040
