(4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

Base Information

Chemical Name:(4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde
CAS No.:143087-42-7
Molecular Formula:C₁₈H₂₂O₄
Molecular Weight:302.37
Hs Code.:

Synonyms:(4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

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Chemical Property of (4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

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Technology Process of (4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

There total 7 articles about (4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-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: 58.0%

: 3375-31-3
palladium diacetate

: 143087-41-6,143234-49-5
[(4aR,6R,9aS)-6-Benzyloxymethyl-octahydro-1,5-dioxa-benzocyclohepten-(2E)-ylidenemethoxy]-tert-butyl-dimethyl-silane

: 143087-42-7
(4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

: 143087-43-8
Acetic acid ((4aR,6R,9aS)-6-benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocyclohepten-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl ester

Guidance literature:: In acetonitrile; at 25 ℃; for 10h;
DOI:10.1016/S0040-4039(00)92095-1

Reference yield: 28.0%

: 143087-41-6,143234-49-5
[(4aR,6R,9aS)-6-Benzyloxymethyl-octahydro-1,5-dioxa-benzocyclohepten-(2E)-ylidenemethoxy]-tert-butyl-dimethyl-silane

: 143087-42-7
(4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

: 143087-43-8
Acetic acid ((4aR,6R,9aS)-6-benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocyclohepten-2-yl)-(tert-butyl-dimethyl-silanyloxy)-methyl ester

Guidance literature:: With palladium diacetate; In acetonitrile; at 25 ℃; for 10h;
DOI:10.1016/S0040-4039(00)92095-1

Reference yield:

: 143087-38-1
(2R,4aR,6R,9aS)-6-Benzyloxymethyl-2-vinyl-octahydro-1,5-dioxa-benzocycloheptene

: 143087-42-7
(4aR,6R,9aS)-6-Benzyloxymethyl-4a,6,7,8,9,9a-hexahydro-4H-1,5-dioxa-benzocycloheptene-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 100 percent / NMO, OsO₄ / tetrahydrofuran; H₂O / 10 h / 25 °C

2: 81 percent / NaIO₄ / methanol; H₂O / 0.25 h / 25 °C

3: 81 percent / CH₂Cl₂ / 10 h / 0 to 25 deg C

4: 58 percent / Pd(OAc)2 / acetonitrile / 10 h / 25 °C

With palladium diacetate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4039(00)92095-1