Technology Process of [(1R,2S,3S,4S,5R,6R)-2,3,4,5-Tetrahydroxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohexyl]-carbamic acid methyl ester
There total 18 articles about [(1R,2S,3S,4S,5R,6R)-2,3,4,5-Tetrahydroxy-6-(7-methoxy-benzo[1,3]dioxol-5-yl)-cyclohexyl]-carbamic acid methyl ester 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 17 steps
1: 1.) n-BuLi / 1.) THF, 2.) THF
2: POCl3, DBU, pyridine
3: H2 / Pd/C
4: H3O(1+), MeOH
5: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C
6: TMSN3, (PhIO)n / CH2Cl2 / -15 °C
7: LiAlH4 / diethyl ether
8: pyridine
9: imidazole / CH2Cl2
10: H3O+
11: t-BuOK / hexamethylphosphoric acid triamide / 90 °C
12: Et3N
14: H2O2, pyridine
15: H2O2, NaHCO3 / methanol; tetrahydrofuran
16: L-selectride / tetrahydrofuran
17: aq. PhCO2Na
With
pyridine; 1H-imidazole; methanol; sodium benzoate; lithium aluminium tetrahydride; n-butyllithium; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1021/ja980407s
- Guidance literature:
-
Multi-step reaction with 15 steps
1: H2 / Pd/C
2: H3O(1+), MeOH
3: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C
4: TMSN3, (PhIO)n / CH2Cl2 / -15 °C
5: LiAlH4 / diethyl ether
6: pyridine
7: imidazole / CH2Cl2
8: H3O+
9: t-BuOK / hexamethylphosphoric acid triamide / 90 °C
10: Et3N
12: H2O2, pyridine
13: H2O2, NaHCO3 / methanol; tetrahydrofuran
14: L-selectride / tetrahydrofuran
15: aq. PhCO2Na
With
pyridine; 1H-imidazole; methanol; sodium benzoate; lithium aluminium tetrahydride; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; triethylamine; lithium chloride;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1021/ja980407s
- Guidance literature:
-
Multi-step reaction with 16 steps
1: POCl3, DBU, pyridine
2: H2 / Pd/C
3: H3O(1+), MeOH
4: lithium (+)-bis(α-methylbenzyl)amide, LiCl / tetrahydrofuran / -78 °C
5: TMSN3, (PhIO)n / CH2Cl2 / -15 °C
6: LiAlH4 / diethyl ether
7: pyridine
8: imidazole / CH2Cl2
9: H3O+
10: t-BuOK / hexamethylphosphoric acid triamide / 90 °C
11: Et3N
13: H2O2, pyridine
14: H2O2, NaHCO3 / methanol; tetrahydrofuran
15: L-selectride / tetrahydrofuran
16: aq. PhCO2Na
With
pyridine; 1H-imidazole; methanol; sodium benzoate; lithium aluminium tetrahydride; trimethylsilylazide; (+)-bis(α-methylbenzyl)amine lithium salt; (PhIO)n; oxonium; potassium tert-butylate; hydrogen; dihydrogen peroxide; L-Selectride; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; trichlorophosphate;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;
DOI:10.1021/ja980407s
