(3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

Base Information

Chemical Name:(3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole
CAS No.:141077-22-7
Molecular Formula:C₂₉H₃₀N₄O₄
Molecular Weight:498.582
Hs Code.:

Synonyms:(3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

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Chemical Property of (3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

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Technology Process of (3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

There total 11 articles about (3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole 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: 79.0%

: 141077-21-6,141195-15-5
(3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-ol

: 141077-22-7
(3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

Guidance literature:: With Zn(N₃)2/bis-pyridine complex; di-isopropyl azodicarboxylate; triphenylphosphine; at 20 ℃; for 1h;
DOI:10.1016/S0040-4039(00)91860-4

Reference yield:

: 53008-65-4,641635-63-4
methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

: 141077-22-7
(3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) (COCl₂)2, 2.) Et₃N / 1.) DMSO, -78 deg C, 2.) -78 deg C to r.t.

2: -40 deg C to r.t.

3: H₂ / Ra/Ni / methanol / Ambient temperature

4: LiAlH₄ / diethyl ether / 0 deg C to r.t.

5: I₂, PPh₃, pyridine / CH₂Cl₂ / 0 °C

6: t-BuOK / tetrahydrofuran / Ambient temperature

7: H₂SO₄ / CHCl₃ / Ambient temperature

8: MeONa / methanol / Ambient temperature

9: 94 percent / NH₂OH, HCl, CH₃ONa / methanol / 3 h / Heating

10: 50 percent / aq. NaOCl / CH₂Cl₂ / 20 h / 20 °C

11: 79 percent / ZnN₆*2py, PPh₃-diisopropyl azodicarboxylate / 1 h / 20 °C

With pyridine; hydrogenchloride; sodium hypochlorite; lithium aluminium tetrahydride; Zn(N₃)2/bis-pyridine complex; di-isopropyl azodicarboxylate; (COCl₂)2; sulfuric acid; potassium tert-butylate; hydrogen; hydroxylamine; iodine; sodium methylate; triethylamine; triphenylphosphine; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform;
DOI:10.1016/S0040-4039(00)91860-4

Reference yield:

: 83051-88-1
methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 141077-22-7
(3aR,5S,6R,7S,8S)-5-Azido-6,7,8-tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazole

Guidance literature:: Multi-step reaction with 10 steps

1: -40 deg C to r.t.

2: H₂ / Ra/Ni / methanol / Ambient temperature

3: LiAlH₄ / diethyl ether / 0 deg C to r.t.

4: I₂, PPh₃, pyridine / CH₂Cl₂ / 0 °C

5: t-BuOK / tetrahydrofuran / Ambient temperature

6: H₂SO₄ / CHCl₃ / Ambient temperature

7: MeONa / methanol / Ambient temperature

8: 94 percent / NH₂OH, HCl, CH₃ONa / methanol / 3 h / Heating

9: 50 percent / aq. NaOCl / CH₂Cl₂ / 20 h / 20 °C

10: 79 percent / ZnN₆*2py, PPh₃-diisopropyl azodicarboxylate / 1 h / 20 °C

With pyridine; hydrogenchloride; sodium hypochlorite; lithium aluminium tetrahydride; Zn(N₃)2/bis-pyridine complex; di-isopropyl azodicarboxylate; sulfuric acid; potassium tert-butylate; hydrogen; hydroxylamine; iodine; sodium methylate; triphenylphosphine; nickel; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform;
DOI:10.1016/S0040-4039(00)91860-4