Technology Process of (2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-carbaldehyde
There total 10 articles about (2R,3R,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-carbaldehyde which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
dipyridinium dichromate; 3 A molecular sieve;
In
dichloromethane;
DOI:10.1021/jo00370a040
- Guidance literature:
-
Multi-step reaction with 10 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
With
pyridine; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; 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 8 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
With
pyridine; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; 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
![[(2S,3R,4R,5S)-3,4-Bis-benzyloxy-5-((E)-(4R,5S)-5-benzyloxymethoxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-ylmethoxy]-tert-butyl-diphenyl-silane](/Databaselist/images/loading.webp)
