Technology Process of (2S,3S,4S,5R,6R)-Methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-3-((2R,3R,4R,5R,6R)-6-(acetoxyMethyl)-3-azido-4,5-bis(benzyloxy)tertrahydro-2H-pyran-2-yloxy)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-carboxylate
There total 26 articles about (2S,3S,4S,5R,6R)-Methyl 6-((1R,2S,3R,4R,5R)-3-acetoxy-4-azido-6,8-dioxabicyclo[3,2,1]octan-2-yloxy)-3-((2R,3R,4R,5R,6R)-6-(acetoxyMethyl)-3-azido-4,5-bis(benzyloxy)tertrahydro-2H-pyran-2-yloxy)-4,5-bis(benzyloxy)tetrahydro-2H-pyran-2-carboxylate 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:
-
O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose;
With
t-butyldimethylsiyl triflate;
In
tert-butyl methyl ether;
at -35 - 45 ℃;
for 2.25h;
Inert atmosphere;
Molecular sieve;
O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate;
In
tert-butyl methyl ether; toluene;
at -35 - -25 ℃;
for 1.5h;
Inert atmosphere;
Molecular sieve;
With
acetic anhydride; triethylamine;
In
tert-butyl methyl ether; toluene;
at -35 - 50 ℃;
for 6h;
Inert atmosphere;
- Guidance literature:
-
With
silver trifluoromethanesulfonate;
In
dichloromethane;
at 0 ℃;
for 3h;
Temperature;
Solvent;
Reagent/catalyst;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: trifluoroacetic acid / dichloromethane; water / 0.33 h / 20 °C
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 5 h / 20 °C
3.1: potassium hydrogencarbonate / N,N-dimethyl-formamide / 4 h / 0 - 20 °C
4.1: pyridine / dichloromethane / 6 h / 0 - 20 °C
5.1: iodine(I) bromide / dichloromethane / 4 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
6.2: 96 h / 20 °C / Molecular sieve; Inert atmosphere
7.1: thiourea / methanol; chloroform / 24 h / 60 °C
8.1: toluene / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
8.2: 2 h / -20 - 20 °C / Molecular sieve; Inert atmosphere
With
pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; iodine(I) bromide; potassium hydrogencarbonate; thiourea; trifluoroacetic acid;
In
methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/cmdc.201400019
