(1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

Base Information

Chemical Name:(1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol
CAS No.:212609-09-1
Molecular Formula:C₂₂H₂₇NO₄
Molecular Weight:369.461
Hs Code.:

Synonyms:(1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

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Chemical Property of (1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

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Technology Process of (1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

There total 8 articles about (1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-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: 100.0%

: 212609-08-0
(1aS,7aR,8R,9S,9aS)-8,9-bis(benzyloxy)octahydro[1,3]oxazolo[3,4-a]oxireno[2,3-e]azocin-5-one

: 212609-09-1
(1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

Guidance literature:: With lithium hydroxide; In ethanol; water; at 94 ℃; for 18h;
DOI:10.1021/jo0012748

Reference yield:

: (9R,10R,10aR)-9,10-dihydroxy-1,5,6,9,10,10a-hexahydro[1,3]oxazolo[3,4-a]azocin-3-one

: 212609-09-1
(1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / KH; tetra-n-butylammonium iodide / tetrahydrofuran / 2 h / 50 °C

2: 75 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 6 h / 20 °C

3: 100 percent / lithium hydroxide / ethanol; H₂O / 18 h / 94 °C

With lithium hydroxide; tetra-(n-butyl)ammonium iodide; potassium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; water;
DOI:10.1021/jo0012748

Reference yield:

: (3aR,11aR,11bR)-2,2-dimethyl-3a,6,7,11,11a,11b-hexahydro[1,3]dioxolo[4,5-c][1,3]oxazolo[3,4-a]azocin-9-one

: 212609-09-1
(1S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(hydroxymethyl)hexahydro-1H-pyrrolizin-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / conc. HBr / acetonitrile / 1 h / 20 °C

2: 84 percent / KH; tetra-n-butylammonium iodide / tetrahydrofuran / 2 h / 50 °C

3: 75 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 6 h / 20 °C

4: 100 percent / lithium hydroxide / ethanol; H₂O / 18 h / 94 °C

With lithium hydroxide; hydrogen bromide; tetra-(n-butyl)ammonium iodide; potassium hydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo0012748