Technology Process of (6S,7S,8S,9R)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-ol
There total 20 articles about (6S,7S,8S,9R)-9-<<(Benzyloxy)carbonyl>amino>-7,8-bis<(methoxymethyl)oxy>tridec-1-en-6-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 8 steps
1: 61 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature
2: 71 percent / H2 / 10percent Pd/C / methanol / 3 h
3: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
4: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min
5: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
6: 68 percent / 0.14 M Zn(BH4)2 / diethyl ether / 0.75 h / 0 °C
7: hydrazine hydrate / ethanol / 2 h / Heating
8: aq. Na2CO3 / CH2Cl2 / 0.08 h / 0 °C
With
zinc(II) tetrahydroborate; oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja00186a038
- Guidance literature:
-
Multi-step reaction with 7 steps
1: 71 percent / H2 / 10percent Pd/C / methanol / 3 h
2: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
3: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min
4: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
5: 68 percent / 0.14 M Zn(BH4)2 / diethyl ether / 0.75 h / 0 °C
6: hydrazine hydrate / ethanol / 2 h / Heating
7: aq. Na2CO3 / CH2Cl2 / 0.08 h / 0 °C
With
zinc(II) tetrahydroborate; oxalyl dichloride; hydrogen; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide;
palladium on activated charcoal;
In
methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja00186a038
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 1 M LiBH(sec-Bu)3 / tetrahydrofuran / 1 h / -78 °C
2: 61 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature
3: 71 percent / H2 / 10percent Pd/C / methanol / 3 h
4: 94 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
5: 1.) Mg / 1.) THF, 2.) THF, -78 deg C, 30 min
6: 85 percent / oxalyl chloride, dimethyl sulfoxide / CH2Cl2 / 1 h / -78 °C
7: 68 percent / 0.14 M Zn(BH4)2 / diethyl ether / 0.75 h / 0 °C
8: hydrazine hydrate / ethanol / 2 h / Heating
9: aq. Na2CO3 / CH2Cl2 / 0.08 h / 0 °C
With
zinc(II) tetrahydroborate; oxalyl dichloride; hydrogen; L-Selectride; sodium carbonate; hydrazine hydrate; magnesium; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane;
DOI:10.1021/ja00186a038
