(1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

Base Information

Chemical Name:(1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran
CAS No.:108032-50-4
Molecular Formula:C₂₉H₄₄O₃
Molecular Weight:440.667
Hs Code.:

Synonyms:(1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

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Chemical Property of (1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

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Technology Process of (1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

There total 7 articles about (1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran 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: 20.7%

: 2216-51-5
(-)-menthol

: 107953-15-1,107953-16-2,138808-89-6,138808-90-9
(3aR*,7S*,7aS*)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-hydroxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

: 108032-50-4
(1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

: 107953-17-3
(1R,3aS,7R,7aR)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

Guidance literature:: With camphor-10-sulfonic acid; In benzene; for 0.5h; Yield given;
DOI:10.1248/cpb.39.2540

Reference yield:

: 138703-08-9
6-Benzyloxy-3-methyl-1,3-hexadiene

: 108032-50-4
(1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

Guidance literature:: Multi-step reaction with 7 steps

1: 97.2 percent / hydroquinone / benzene / 19 h / Heating

2: 1) NaHCO₃, 2) KI, I₂ / 1) water, 2 h, r.t., 2) water, 17 h, r.t.

3: 4.58 g / BH₃*Me₂S, B(OMe)3 / tetrahydrofuran / 7 h / Ambient temperature

4: 63 percent / Zn-dust, AcOH / 1 h / 90 °C

5: 1) LDA / 1) THF, -65 deg C, 30 min, 2) -65 deg C, 4 h

6: 77.4 percent / i-Bu₂AlH / tetrahydrofuran; toluene / 1 h / -65 °C

7: CSA / benzene / 0.5 h

With Trimethyl borate; dimethylsulfide borane complex; camphor-10-sulfonic acid; iodine; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; hydroquinone; potassium iodide; zinc; lithium diisopropyl amide; In tetrahydrofuran; toluene; benzene;
DOI:10.1248/cpb.39.2540

Reference yield:

: 107953-12-8,138808-87-4
(3aR*,7S*,7aS*)-7-(2-Benzyloxy)ethyl-6-methyl-3a,4,7,7a-tetrahydrophthalide

: 108032-50-4
(1S,3aR,7S,7aS)-7-(2-Benzyloxy)ethyl-6,7a-dimethyl-1-l-menthoxy-3a,4,7,7a-tetrahydro-(1,3H)-isobenzofuran

Guidance literature:: Multi-step reaction with 3 steps

1: 1) LDA / 1) THF, -65 deg C, 30 min, 2) -65 deg C, 4 h

2: 77.4 percent / i-Bu₂AlH / tetrahydrofuran; toluene / 1 h / -65 °C

3: CSA / benzene / 0.5 h

With camphor-10-sulfonic acid; diisobutylaluminium hydride; lithium diisopropyl amide; In tetrahydrofuran; toluene; benzene;
DOI:10.1248/cpb.39.2540