Technology Process of Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxymethoxy-3,3-dimethyl-tetrahydro-pyran-4-yl ester
There total 15 articles about Benzoic acid (2R,4R,6S)-2-((S)-2,3-dimethoxy-propyl)-6-methoxymethoxy-3,3-dimethyl-tetrahydro-pyran-4-yl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 14 steps
1: Imidazole / dimethylformamide
2: CSA / benzene / 72percent overall yield from INO 660
3: PPTS / CH2Cl2
4: LDA / tetrahydrofuran / -78 °C
5: CSA / CH2Cl2; methanol / 38percent yield from INO 690; yield of byproduct (INO 760): 37percent from INO 690
6: PCC, 3A-MS / CH2Cl2
7: L-Selectride / tetrahydrofuran / -78 °C / 90percent yield from INO 760
8: 83 percent / BF3:Et2O / -30 °C
9: 83 percent / Silica gel / diethyl ether
10: DIBAH / toluene / -78 °C
11: 88 percent / i-Pr2NEt / CH2Cl2 / Heating; 88percent yield from INO 820
12: 87 percent / NBS, AgNO3, Na2CO3 / H2O; acetonitrile
13: 98 percent / LiAlH4 / diethyl ether / 0 °C
14: 100 percent / Pyridine
With
pyridine; 1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; silica gel; L-Selectride; diisobutylaluminium hydride; sodium carbonate; silver nitrate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)99027-0
- Guidance literature:
-
Multi-step reaction with 15 steps
1: p-TsOH / methanol
2: Imidazole / dimethylformamide
3: CSA / benzene / 72percent overall yield from INO 660
4: PPTS / CH2Cl2
5: LDA / tetrahydrofuran / -78 °C
6: CSA / CH2Cl2; methanol / 38percent yield from INO 690; yield of byproduct (INO 760): 37percent from INO 690
7: PCC, 3A-MS / CH2Cl2
8: L-Selectride / tetrahydrofuran / -78 °C / 90percent yield from INO 760
9: 83 percent / BF3:Et2O / -30 °C
10: 83 percent / Silica gel / diethyl ether
11: DIBAH / toluene / -78 °C
12: 88 percent / i-Pr2NEt / CH2Cl2 / Heating; 88percent yield from INO 820
13: 87 percent / NBS, AgNO3, Na2CO3 / H2O; acetonitrile
14: 98 percent / LiAlH4 / diethyl ether / 0 °C
15: 100 percent / Pyridine
With
pyridine; 1H-imidazole; N-Bromosuccinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; silica gel; L-Selectride; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid; silver nitrate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
DOI:10.1016/S0040-4039(00)99027-0
