(1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Base Information

Chemical Name:(1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene
CAS No.:741259-18-7
Molecular Formula:C₃₁H₄₂O₄
Molecular Weight:478.672
Hs Code.:

Synonyms:(1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Chemical Property of (1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

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Technology Process of (1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

There total 10 articles about (1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene 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: 80.0%

: 741259-16-5
1α,6α-di-(4-methoxy-benzyloxy)-10-epi-eudesm-4(5)-en-3-one

: 741259-18-7
(1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: 1α,6α-di-(4-methoxy-benzyloxy)-10-epi-eudesm-4(5)-en-3-one; With acetic acid; toluene-4-sulfonic acid hydrazide; at 20 ℃; for 10h;

With sodium tetrahydroborate; In acetic acid; for 0.5h; Further stages.;
DOI:10.1016/j.tet.2004.05.056

Reference yield:

: 6485-40-1,2244-16-8
(R)-Carvone

: 741259-18-7
(1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 12 steps

1.1: H₂ / Pd/C / ethanol / 30 h

1.2: 90 percent / NEt₃ / dimethylformamide / 48 h / Heating

2.1: 670 mg / TiCl₄ / CH₂Cl₂ / -78 - -40 °C

3.1: 85 percent / p-TsOH / CH₂Cl₂ / 24 h / 20 °C

4.1: NaOH / methanol / 3 h / 0 °C

5.1: 1.06 g / PCC; pyridine; SiO₂ / CH₂Cl₂ / 20 °C

6.1: tetrahydrofuran / 0.5 h / -78 °C

7.1: 880 mg / PCC; pyridine; SiO₂ / CH₂Cl₂ / 48 h / 20 °C

8.1: NaOMe / methanol / 2 h / 20 °C

8.2: 87 percent / MsCl; NEt₃ / CH₂Cl₂ / 8 h / 20 °C

9.1: 82 percent / NaOAc; DMAP / 0.33 h / Heating

10.1: 83 percent / m-CPBA / CH₂Cl₂ / 24 h / 20 °C

11.1: 82 percent / p-TsOH / CH₂Cl₂ / 24 h / 20 °C

12.1: TsNHNH₂; AcOH / 10 h / 20 °C

12.2: 80 percent / NaBH₄ / acetic acid / 0.5 h

With pyridine; dmap; sodium hydroxide; hydrogen; sodium methylate; sodium acetate; silica gel; titanium tetrachloride; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; pyridinium chlorochromate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2.1: Mukaiyama aldol reaction;
DOI:10.1016/j.tet.2004.05.056

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 741259-18-7
(1S,2S,4aS,5S)-2-Isopropyl-1,5-bis-(4-methoxy-benzyloxy)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 85 percent / p-TsOH / CH₂Cl₂ / 24 h / 20 °C

2.1: NaOH / methanol / 3 h / 0 °C

3.1: 1.06 g / PCC; pyridine; SiO₂ / CH₂Cl₂ / 20 °C

4.1: tetrahydrofuran / 0.5 h / -78 °C

5.1: 880 mg / PCC; pyridine; SiO₂ / CH₂Cl₂ / 48 h / 20 °C

6.1: NaOMe / methanol / 2 h / 20 °C

6.2: 87 percent / MsCl; NEt₃ / CH₂Cl₂ / 8 h / 20 °C

7.1: 82 percent / NaOAc; DMAP / 0.33 h / Heating

8.1: 83 percent / m-CPBA / CH₂Cl₂ / 24 h / 20 °C

9.1: 82 percent / p-TsOH / CH₂Cl₂ / 24 h / 20 °C

10.1: TsNHNH₂; AcOH / 10 h / 20 °C

10.2: 80 percent / NaBH₄ / acetic acid / 0.5 h

With pyridine; dmap; sodium hydroxide; sodium methylate; sodium acetate; silica gel; toluene-4-sulfonic acid; acetic acid; 3-chloro-benzenecarboperoxoic acid; toluene-4-sulfonic acid hydrazide; pyridinium chlorochromate; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tet.2004.05.056