(1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

Base Information

Chemical Name:(1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one
CAS No.:537030-25-4
Molecular Formula:C₂₉H₃₁NO₅
Molecular Weight:473.569
Hs Code.:

Synonyms:(1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

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Chemical Property of (1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

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Technology Process of (1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

There total 11 articles about (1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one 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: 80.0%

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

: 537030-25-4
(1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

Guidance literature:: With water; acetic acid; zinc; at 50 ℃; for 4h;
DOI:10.1016/S0040-4039(03)00239-9

Reference yield:

: 100-44-7
benzyl chloride

: 537030-25-4
(1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

Guidance literature:: Multi-step reaction with 6 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

6.1: 80 percent / Zn; CH₃COOH; water / 4 h / 50 °C

With 1H-imidazole; methanol; sulfuric acid; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; water; iodine; acetic acid; sodium sulfate; triphenylphosphine; zinc; 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

: 537030-25-4
(1R,2R,3R,6R,7aR)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one

Guidance literature:: Multi-step reaction with 6 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

6.1: 80 percent / Zn; CH₃COOH; water / 4 h / 50 °C

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