(1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

Base Information

Chemical Name:(1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester
CAS No.:132164-31-9
Molecular Formula:C₂₂H₂₈O₅
Molecular Weight:372.461
Hs Code.:

Synonyms:(1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

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Chemical Property of (1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

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Technology Process of (1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

There total 8 articles about (1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester 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:

: Acetic acid (3R,3aS,6S,8S,8aS,9S)-6,9-dihydroxy-5-methoxy-3-methyl-2,3,6,7,8,8a-hexahydro-1H-3a,7-methano-azulen-8-ylmethyl ester

: 132164-31-9
(1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 14.5 h / Ambient temperature

2: sat. aq. oxalic acid / methanol / 5 h / 40 - 45 °C

3: pyridine / 18 h / Ambient temperature

4: 2) NaH / 1) THF, room temp., 1.5 h, 2) DMF, room temp., 35 h

5: 1) PCC, 2) Pb(OAc)4 / 1) CH₂Cl₂, room temp., 3.5 h, 2) MeOH, room temp, 50 min

With pyridine; lead(IV) acetate; oxalic acid; sodium hydride; pyridinium chlorochromate; In methanol;
DOI:10.1016/S0040-4039(00)97269-1

Reference yield:

: 123298-33-9
Acetic acid (E)-6-(2-hydroxy-4,5-dimethoxy-phenyl)-hept-2-enyl ester

: 132164-31-9
(1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / LiClO₄ / methanol; acetic acid; toluene / anodic oxidation

2: DIBAL-H / tetrahydrofuran / a) -70 deg C, 45 min, b) room temp., 45 min

3: pyridine / 14.5 h / Ambient temperature

4: sat. aq. oxalic acid / methanol / 5 h / 40 - 45 °C

5: pyridine / 18 h / Ambient temperature

6: 2) NaH / 1) THF, room temp., 1.5 h, 2) DMF, room temp., 35 h

7: 1) PCC, 2) Pb(OAc)4 / 1) CH₂Cl₂, room temp., 3.5 h, 2) MeOH, room temp, 50 min

With pyridine; lead(IV) acetate; lithium perchlorate; oxalic acid; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; methanol; acetic acid; toluene;
DOI:10.1016/S0040-4039(00)97269-1

Reference yield:

: 132164-28-4
Acetic acid (3S,3aR,6R,8R,8aR,9R)-6-acetoxy-8-acetoxymethyl-5-methoxy-3-methyl-2,3,6,7,8,8a-hexahydro-1H-3a,7-methano-azulen-9-yl ester

: 132164-31-9
(1S,2S,3aS,4R,6aS)-1-Benzyloxymethyl-4-methyl-3-oxo-3a-(2-oxo-propyl)-octahydro-pentalene-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: sat. aq. oxalic acid / methanol / 5 h / 40 - 45 °C

2: pyridine / 18 h / Ambient temperature

3: 2) NaH / 1) THF, room temp., 1.5 h, 2) DMF, room temp., 35 h

4: 1) PCC, 2) Pb(OAc)4 / 1) CH₂Cl₂, room temp., 3.5 h, 2) MeOH, room temp, 50 min

With pyridine; lead(IV) acetate; oxalic acid; sodium hydride; pyridinium chlorochromate; In methanol;
DOI:10.1016/S0040-4039(00)97269-1