1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

Base Information

Chemical Name:1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose
CAS No.:133886-05-2
Molecular Formula:C₁₆H₁₉N₃O₆
Molecular Weight:349.343
Hs Code.:

Synonyms:1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

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Chemical Property of 1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

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Technology Process of 1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

There total 2 articles about 1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose 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:

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

: 133886-05-2
1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 2.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96124-1

Reference yield:

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

: 133886-05-2
1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / 1) (COCl)2, DMSO, 2) Et₃N / CH₂Cl₂ / 1) -60 deg C, 50 min, 2) a) -60 deg , 20 min, b) 0 deg C, 80 min

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

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(01)96124-1

Reference yield:

: 133886-05-2
1-β-Azido-1-dehydro-1-α-carboxy-1-deoxy-2,3-O-isopropylidene-5-O-benzyl-D-ribofuranose

: 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 8 steps

1: ClCOOEt, NEt₃ / tetrahydrofuran / 0.17 h

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

3: acetonitrile

4: acetonitrile / 5 h / Ambient temperature

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

6: 92 percent / Dowex 50W(H+) / methanol; H₂O / 0.17 h / 60 °C

7: 96 percent / N₂H₄*H₂O / methanol / 1 h / Ambient temperature

8: 93 percent / H₂ / Pd-C (10percent) / methanol / 15 h / 55 °C / 2574.3 Torr

With pyridine; dmap; Dowex 50W(H+); ammonia; hydrogen; chloroformic acid ethyl ester; hydrazine hydrate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; acetonitrile;
DOI:10.1016/S0040-4020(01)96124-1