2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

Base Information

Chemical Name:2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose
CAS No.:133886-04-1
Molecular Formula:C₁₆H₁₉N₃O₅
Molecular Weight:333.344
Hs Code.:

Synonyms:2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

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Chemical Property of 2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

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Technology Process of 2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

There total 2 articles about 2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose 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:

Reference yield: 96.0%

: 133886-01-8
2-azido-2-deoxy-6-O-benzyl-3,4-O-isopropylidene-β-D-psico-furanose

: 133886-04-1
2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1) -60 deg C, 50 min, 2) a) -60 deg , 20 min, b) 0 deg C, 80 min;
DOI:10.1016/S0040-4020(01)96124-1

Reference yield:

: 2-((3aR,4S,6R,6aR)-4-Azido-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-3-methyl-thiazolidine

: 133886-04-1
2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

: azido 6-O-benzyl-3,4-O-isopropylidene-β-D-ribo-2-hexosulofuranoside hydrate

Guidance literature:: With mercury dichloride; In acetonitrile; for 0.25h; Title compound not separated from byproducts;
DOI:10.1021/jo00103a057

Reference yield:

: 133886-04-1
2-β-Azido-2-deoxy-6-O-benzyl-1-didehydro-3,4-O-isopropylidene-D-psicofuranose

: 130607-26-0
[5S-(5α,7α,8β,9β)]-1,3-diaza-8,9-dihydroxy-7-(hydroxymethyl)-6-oxaspiro[4.4]nonane-2,4-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 11.00 g / NaClO₂, NaH₂PO₄*2H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 2.5 h / Ambient temperature

2: ClCOOEt, NEt₃ / tetrahydrofuran / 0.17 h

3: NH₃ gas / tetrahydrofuran / 0.5 h / Ambient temperature

4: acetonitrile

5: acetonitrile / 5 h / Ambient temperature

6: pyridine, 4-N,N-dimethylaminopyridine / 20 h

7: 92 percent / Dowex 50W(H+) / methanol; H₂O / 0.17 h / 60 °C

8: 96 percent / N₂H₄*H₂O / methanol / 1 h / Ambient temperature

9: 93 percent / H₂ / Pd-C (10percent) / methanol / 15 h / 55 °C / 2574.3 Torr

With pyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dowex 50W(H+); ammonia; hydrogen; chloroformic acid ethyl ester; hydrazine hydrate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)96124-1