(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

Base Information

Chemical Name:(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde
CAS No.:114826-90-3
Molecular Formula:C₂₆H₃₂O₅
Molecular Weight:424.537
Hs Code.:

Synonyms:(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

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Chemical Property of (1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

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Technology Process of (1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

There total 6 articles about (1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde 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: 83.0%

: 114826-89-0,114884-17-2
1-[(1R,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethane-1,2-diol

: 114826-90-3
(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

Guidance literature:: With sodium periodate; In water; acetone; for 0.25h; Ambient temperature;
DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

: 34638-25-0,38110-77-9,43119-28-4,54483-22-6,26054-46-6
(1R,5S)-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 114826-90-3
(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 1) H₂SO₄, AcOH; / 1) 60 deg C, 1 day; 2) Amberlite IR-120(H⁺), 70 deg C, 15 h

2: 60 percent / NaH / dimethylformamide

4: 73 percent / LDA, MoOPH / tetrahydrofuran / -78 - 20 °C

5: 69 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

6: 83 percent / NaIO₄ / H₂O; acetone / 0.25 h / Ambient temperature

With sodium periodate; lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; sulfuric acid; sodium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(01)91379-6

Reference yield:

: 114826-79-8
(3aS,4R,5S,6aR)-5-Benzyloxy-4-benzyloxymethyl-hexahydro-cyclopenta[b]furan-2-one

: 114826-90-3
(1S,2R,3S,5R)-3-Benzyloxy-2-benzyloxymethyl-5-(tetrahydro-pyran-2-yloxy)-cyclopentanecarbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

2: 73 percent / LDA, MoOPH / tetrahydrofuran / -78 - 20 °C

3: 69 percent / LiAlH₄ / diethyl ether / 3 h / Ambient temperature

4: 83 percent / NaIO₄ / H₂O; acetone / 0.25 h / Ambient temperature

With sodium periodate; lithium aluminium tetrahydride; MoO₅*pyridine*HMPA; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; water; acetone;
DOI:10.1016/S0040-4039(01)91379-6