Technology Process of (2S,4RS,6E)-2-(benzyloxy)-4-(hydroxymethyl)oct-6-enal dimethyl acetal
There total 10 articles about (2S,4RS,6E)-2-(benzyloxy)-4-(hydroxymethyl)oct-6-enal dimethyl acetal which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: 77.7 percent / Et3N / CH2Cl2 / 20 h / 22 °C
2.1: NaH; [15]crown-5; H2O / benzene / 6 h / Heating
2.2: benzene / 17 °C / Heating
3.1: 22.73 g / DIAD; PPh3 / tetrahydrofuran / 3 h / 23 °C
4.1: 11.72 g / ZnBr2 / methanol; CH2Cl2 / 3 h / 23 °C
5.1: 11.72 g / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.5 h / -78 °C
6.1: 5.885 g / TsOH*H2O / methanol / 1 h / 23 °C
7.1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 5.5 h / 65 °C
8.1: 7.982 g / LiAlH4 / tetrahydrofuran / 16 h / 22 °C
With
lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 15-crown-5; di-isopropyl azodicarboxylate; water; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc dibromide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; benzene;
5.1: Swern's protocol / 7.1: Ireland-Claisen rearrangement;
DOI:10.1002/hlca.200390125
- Guidance literature:
-
With
lithium aluminium tetrahydride;
In
tetrahydrofuran;
at 22 ℃;
for 16h;
DOI:10.1002/hlca.200390125
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 85.1 percent / BH3*SMe2 / tetrahydrofuran / 3 h / 20 °C
2.1: 77.7 percent / Et3N / CH2Cl2 / 20 h / 22 °C
3.1: NaH; [15]crown-5; H2O / benzene / 6 h / Heating
3.2: benzene / 17 °C / Heating
4.1: 22.73 g / DIAD; PPh3 / tetrahydrofuran / 3 h / 23 °C
5.1: 11.72 g / ZnBr2 / methanol; CH2Cl2 / 3 h / 23 °C
6.1: 11.72 g / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 0.5 h / -78 °C
7.1: 5.885 g / TsOH*H2O / methanol / 1 h / 23 °C
8.1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / 5.5 h / 65 °C
9.1: 7.982 g / LiAlH4 / tetrahydrofuran / 16 h / 22 °C
With
lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 15-crown-5; di-isopropyl azodicarboxylate; dimethylsulfide borane complex; water; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; zinc dibromide;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; benzene;
6.1: Swern's protocol / 8.1: Ireland-Claisen rearrangement;
DOI:10.1002/hlca.200390125
