(2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

Base Information

Chemical Name:(2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde
CAS No.:82131-49-5
Molecular Formula:C₂₀H₂₆O₄
Molecular Weight:330.424
Hs Code.:

Synonyms:

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Chemical Property of (2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

Chemical Property:

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Technology Process of (2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

There total 5 articles about (2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde 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:

: 54314-84-0
1-[(3-bromopropoxy)methyl]-benzene

: 82131-49-5,96038-96-9
(2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) Li, 2.) cuprous iodide / 2.) -70 deg C, 1 h, 3.) ether, -70 deg C, 3 h, then up to 20 deg C within 14 h

2: 92 percent / NaBH₄ / methanol / 4 °C

3: 64 percent / dichloroacetic acid / 16 h / Ambient temperature

4: 1.) KMnO₄, benzyltriethylammonium chloride, 2.) sodium acetate, acetic acid / 1.) CH₂Cl₂, 20 deg C, 2 h, 2.) 2 h

With dichloro-acetic acid; sodium tetrahydroborate; potassium permanganate; copper(l) iodide; N-benzyl-N,N,N-triethylammonium chloride; sodium acetate; lithium; acetic acid; In methanol;
DOI:10.1016/0040-4020(81)80013-0

Reference yield:

: 5530-96-1,15584-54-0,61139-01-3,85806-41-3,105500-35-4,111136-75-5,699-82-1,150738-84-4
endo-tricyclo[5.2.1.0(2,6)]deca-4,8-dien-3-one

: 82131-49-5,96038-96-9
(2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) Li, 2.) cuprous iodide / 2.) -70 deg C, 1 h, 3.) ether, -70 deg C, 3 h, then up to 20 deg C within 14 h

2: 92 percent / NaBH₄ / methanol / 4 °C

3: 64 percent / dichloroacetic acid / 16 h / Ambient temperature

4: 1.) KMnO₄, benzyltriethylammonium chloride, 2.) sodium acetate, acetic acid / 1.) CH₂Cl₂, 20 deg C, 2 h, 2.) 2 h

With dichloro-acetic acid; sodium tetrahydroborate; potassium permanganate; copper(l) iodide; N-benzyl-N,N,N-triethylammonium chloride; sodium acetate; lithium; acetic acid; In methanol;
DOI:10.1016/0040-4020(81)80013-0

Reference yield:

: 82131-36-0
5-exo-(3'-benzyloxypropyl)tricyclo<5.2.1.0^2,6>dec-8-en-3-one

: 82131-49-5,96038-96-9
(2aR,4S,4aR,5S,6aS,6bS)-5-(3-Benzyloxy-propyl)-2-hydroxy-octahydro-pentaleno[1,6-bc]furan-4-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / NaBH₄ / methanol / 4 °C

2: 64 percent / dichloroacetic acid / 16 h / Ambient temperature

3: 1.) KMnO₄, benzyltriethylammonium chloride, 2.) sodium acetate, acetic acid / 1.) CH₂Cl₂, 20 deg C, 2 h, 2.) 2 h

With dichloro-acetic acid; sodium tetrahydroborate; potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride; sodium acetate; acetic acid; In methanol;
DOI:10.1016/0040-4020(81)80013-0