Technology Process of 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-decitol
There total 12 articles about 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-gulo-decitol 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:
-
With
2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride;
In
toluene;
at 85 ℃;
for 2h;
Yield given;
DOI:10.1039/a800571k
- Guidance literature:
-
Multi-step reaction with 4 steps
1: 24 percent / ZnBr2 / CH2Cl2 / 5 h / -15 °C
2: NaBH4 / methanol; diethyl ether / 1 h / -20 °C
3: 83 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 70 °C
4: 293 mg / Bu3SnH; AIBN / toluene / 2 h / 85 °C
With
dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; zinc dibromide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
1: glycosylation / 2: Reduction / 3: Esterification / 4: Reduction;
DOI:10.1021/jo981861h
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 96 percent / 10-camphorsulfonic acid / CH2Cl2 / 1.5 h / 0 - 20 °C
2: 96 percent / n-Bu4NF*3H2O / tetrahydrofuran / 6 h / 20 °C
3: 94 percent / 4-Angstroem molecular sieves; pyridinium chlorochromate / CH2Cl2 / 0.33 h / 20 °C
4: 82 percent / 4-Angstroem molecular sieves; triethylamine / CH2Cl2 / 1 h / -15 °C
5: 24 percent / ZnBr2 / CH2Cl2 / 5 h / -15 °C
6: NaBH4 / methanol; diethyl ether / 1 h / -20 °C
7: 83 percent / 4-(N,N-dimethylamino)pyridine / tetrahydrofuran / 6 h / 70 °C
8: 293 mg / Bu3SnH; AIBN / toluene / 2 h / 85 °C
With
dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethylamine; pyridinium chlorochromate; zinc dibromide;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
1: Cyclization / 2: desilylation / 3: Oxidation / 4: silylation / 5: glycosylation / 6: Reduction / 7: Esterification / 8: Reduction;
DOI:10.1021/jo981861h
![(R)-4-[1-(Imidazole-1-carbothioyloxy)-2-((2R,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester](/Databaselist/images/loading.webp)
