Technology Process of methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-6,7,13-trideoxy-α-L-glycero-D-gluco-D-gluco-tridec-6-eno-1,5-pyranoside
There total 6 articles about methyl 8,12-anhydro-2,3,4,9,10,11-hexa-O-benzyl-6,7,13-trideoxy-α-L-glycero-D-gluco-D-gluco-tridec-6-eno-1,5-pyranoside 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:
-
(methyl 2,3,4-tri-O-benzyl-6-deoxy-D-glucopyranosid-6-yl)triphenylphosphonium iodide;
With
n-butyllithium;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane;
at -30 ℃;
for 0.0833333h;
2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-aldehydo-L-glycero-D-gluco-heptose;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane;
at -30 - -10 ℃;
for 2h;
DOI:10.1021/jo049406a
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 97 percent / pyridinium chlorochromate
2.1: nBuLi / diethyl ether; hexane / 1 h / -78 - -75 °C
2.2: 93 percent / diethyl ether; hexane / 1.5 h / -75 - -65 °C
3.1: 93 percent / triethylamine / CH2Cl2 / 42 h / 20 °C
4.1: 93 percent / samarium(II) iodide; ethylene glycol / tetrahydrofuran / 0.17 h
5.1: methyl triflate / acetonitrile / 0.25 h / 20 °C
5.2: NaBH4 / methanol / 0.17 h / 20 °C
5.3: AgNO3; H2O / acetonitrile / 0.17 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.08 h / -30 °C
6.2: 37 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -30 - -10 °C
With
n-butyllithium; samarium diiodide; ethylene glycol; triethylamine; pyridinium chlorochromate; methyl trifluoromethanesulfonate;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetonitrile;
6.2: Wittig reaction;
DOI:10.1021/jo049406a
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: nBuLi / diethyl ether; hexane / 1 h / -78 - -75 °C
1.2: 93 percent / diethyl ether; hexane / 1.5 h / -75 - -65 °C
2.1: 93 percent / triethylamine / CH2Cl2 / 42 h / 20 °C
3.1: 93 percent / samarium(II) iodide; ethylene glycol / tetrahydrofuran / 0.17 h
4.1: methyl triflate / acetonitrile / 0.25 h / 20 °C
4.2: NaBH4 / methanol / 0.17 h / 20 °C
4.3: AgNO3; H2O / acetonitrile / 0.17 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.08 h / -30 °C
5.2: 37 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 2 h / -30 - -10 °C
With
n-butyllithium; samarium diiodide; ethylene glycol; triethylamine; methyl trifluoromethanesulfonate;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; acetonitrile;
5.2: Wittig reaction;
DOI:10.1021/jo049406a
