(2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

Base Information

Chemical Name:(2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one
CAS No.:337309-32-7
Molecular Formula:C₁₈H₂₄O₆
Molecular Weight:336.385
Hs Code.:

Synonyms:(2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

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Chemical Property of (2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

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Technology Process of (2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

There total 7 articles about (2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-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: 95.0%

: 337309-22-5
(2R,4aR,6S,9R,10aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

: 337309-32-7
(2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1039/b009506k

Reference yield:

: 337309-17-8
[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-acetic acid tert-butyl ester

: 337309-32-7
(2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

Guidance literature:: Multi-step reaction with 7 steps

1: 40 percent / LDA / tetrahydrofuran / 0.17 h / -78 °C

2: 60 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / Heating

3: 98 percent / LiAlH₄ / tetrahydrofuran / 5 h / 0 - 20 °C

4: 88 percent / NEt₃; DMAP / CH₂Cl₂ / 16 h / 20 °C

5: 79 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.5 h / -60 °C

6: 74 percent / diethyl ether / 0.5 h / -78 °C

7: 95 percent / TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; 5: Swern oxidation;
DOI:10.1039/b009506k

Reference yield:

: 337309-18-9
(R)-2-[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-3-hydroxy-pent-4-enoic acid tert-butyl ester

: 337309-32-7
(2R,4aR,6S,9R,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-hexahydro-1,3,5-trioxa-benzocycloocten-7-one

Guidance literature:: Multi-step reaction with 6 steps

1: 60 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 24 h / Heating

2: 98 percent / LiAlH₄ / tetrahydrofuran / 5 h / 0 - 20 °C

3: 88 percent / NEt₃; DMAP / CH₂Cl₂ / 16 h / 20 °C

4: 79 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 0.5 h / -60 °C

5: 74 percent / diethyl ether / 0.5 h / -78 °C

6: 95 percent / TBAF; AcOH / tetrahydrofuran / 5 h / 20 °C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; acetic acid; dimethyl sulfoxide; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; 4: Swern oxidation;
DOI:10.1039/b009506k