(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

Base Information

Chemical Name:(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide
CAS No.:537030-24-3
Molecular Formula:C₃₁H₃₆N₂O₅
Molecular Weight:516.637
Hs Code.:

Synonyms:(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

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Chemical Property of (2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

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Technology Process of (2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

There total 11 articles about (2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide 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: 85.0%

: 2680-03-7,68761-83-1
N,N-Dimethylacrylamide

: 537030-19-6
(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

: 537030-24-3
(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

Guidance literature:: In dichloromethane; at 20 ℃; for 72h; stereoselective reaction;
DOI:10.1002/ejoc.201000632

Reference yield:

: 100-44-7
benzyl chloride

: 537030-24-3
(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: MeOH; H₂SO₄; Na₂SO₄ / 21 h / 20 °C

1.2: KOH; Na₂SO₄ / 8 h / Heating

1.3: 50 percent / HCl; water; CH₃COOH / 60 - 70 °C

2.1: NH₂OH*HCl / pyridine / 24 h / 20 °C

2.2: pyridine / 18 h / 20 °C

3.1: 48 percent / I₂; ImH; Ph₃P / toluene / 1 h / Heating

4.1: 91 percent / TBAF on silica gel / benzene / 1.5 h / Heating

5.1: 78 percent / CH₂Cl₂ / 20 °C

With 1H-imidazole; methanol; sulfuric acid; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; iodine; sodium sulfate; triphenylphosphine; In pyridine; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4039(03)00239-9

Reference yield:

: 532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7
D-arabinofuranose

: 537030-24-3
(2R,3aR,4R,5R,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-N,N-dimethylhexahydropyrrolo[1,2-b]isoxazole-2-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: MeOH; H₂SO₄; Na₂SO₄ / 21 h / 20 °C

1.2: KOH; Na₂SO₄ / 8 h / Heating

1.3: 50 percent / HCl; water; CH₃COOH / 60 - 70 °C

2.1: NH₂OH*HCl / pyridine / 24 h / 20 °C

2.2: pyridine / 18 h / 20 °C

3.1: 48 percent / I₂; ImH; Ph₃P / toluene / 1 h / Heating

4.1: 91 percent / TBAF on silica gel / benzene / 1.5 h / Heating

5.1: 78 percent / CH₂Cl₂ / 20 °C

With 1H-imidazole; methanol; sulfuric acid; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; iodine; sodium sulfate; triphenylphosphine; In pyridine; dichloromethane; toluene; benzene;
DOI:10.1016/S0040-4039(03)00239-9