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

Base Information

Chemical Name:(3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-ol
CAS No.:141077-21-6
Molecular Formula:C₂₉H₃₁NO₅
Molecular Weight:473.569
Hs Code.:

Synonyms:

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

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

There total 10 articles about (3aR,5R,6R,7R,8S)-6,7,8-Tris-benzyloxy-3a,4,5,6,7,8-hexahydro-3H-cyclohepta[c]isoxazol-5-ol 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: 3.0%

: 141077-09-0,141946-50-1
(2S,3R,4R,5R)-2,3,4-Tris-benzyloxy-5-hydroxy-oct-7-enal oxime

: 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

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

Guidance literature:: With sodium hypochlorite; In dichloromethane; at 20 ℃; for 20h;
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

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

Guidance literature:: Multi-step reaction with 10 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

With pyridine; hydrogenchloride; sodium hypochlorite; lithium aluminium tetrahydride; (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

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

Guidance literature:: Multi-step reaction with 9 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

With pyridine; hydrogenchloride; sodium hypochlorite; lithium aluminium tetrahydride; 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