1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

Base Information

Chemical Name:1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one
CAS No.:323192-59-2
Molecular Formula:C₂₅H₃₈O₅
Molecular Weight:418.574
Hs Code.:

Synonyms:1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

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Chemical Property of 1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

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Technology Process of 1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

There total 5 articles about 1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-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:

: 1-{(4R,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-ol

: 323192-59-2
1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; for 1h;
DOI:10.1021/ja0035102

Reference yield:

: 1025997-26-5
(E)-(3S,4S)-7,7-Diethoxy-2,4-dimethyl-hept-5-en-3-ol

: 323192-59-2
1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: KH / tetrahydrofuran / 16 h

1.2: pyridinium p-toluenesulfonic acid / acetone; H₂O / 1 h / Heating

2.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / -78 - 20 °C

2.2: diethyl ether / 3 h / -90 - 20 °C

2.3: 71 percent / NaOH; H₂O₂ / diethyl ether; H₂O / 1 h / Heating

3.1: HgClOAc; Yb(OTf)3 / -78 - 0 °C

3.2: DABCO; tris(2,4-di-tert-butylphenyl)phosphite; H₂ / Rh(acac)(CO)2 / ethyl acetate / 24 h / 50 °C / 41372.9 Torr

4.1: diethyl ether / 0.5 h / 0 °C

5.1: 0.35 g / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With (+)-Ipc₂BOMe; potassium hydride; chloro(acetato)mercury(II); Dess-Martin periodane; ytterbium(III) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Brown's asymmetric allylation;
DOI:10.1021/ja0035102

Reference yield:

: 323192-62-7
(4S,5S)-4,6-dimethyl-5-(p-methoxybenzyloxy)-trans-hept-2-enal

: 323192-59-2
1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / -78 - 20 °C

1.2: diethyl ether / 3 h / -90 - 20 °C

1.3: 71 percent / NaOH; H₂O₂ / diethyl ether; H₂O / 1 h / Heating

2.1: HgClOAc; Yb(OTf)3 / -78 - 0 °C

2.2: DABCO; tris(2,4-di-tert-butylphenyl)phosphite; H₂ / Rh(acac)(CO)2 / ethyl acetate / 24 h / 50 °C / 41372.9 Torr

3.1: diethyl ether / 0.5 h / 0 °C

4.1: 0.35 g / Dess-Martin periodinane / CH₂Cl₂ / 1 h

With (+)-Ipc₂BOMe; chloro(acetato)mercury(II); Dess-Martin periodane; ytterbium(III) triflate; In diethyl ether; dichloromethane; 1.1: Brown's asymmetric allylation;
DOI:10.1021/ja0035102