(1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene

Base Information

• Chemical Name: (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene
• CAS No.: 213026-15-4
• Molecular Formula: C₂₆H₃₈O₆
• Molecular Weight: 446.584
• Mol file: 213026-15-4.mol

Synonyms:(1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene

Chemical Property of (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene

There total 17 articles about (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-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: 98.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (1S,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)naphthalene-2-one (213026-14-3) → (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene (213026-15-4)

Guidance literature:

With potassium tert-butylate; In toluene; Heating;

DOI:10.1002/(SICI)1521-3773(19991216)38:24<3710::AID-ANIE3710>3.0.CO;2-H

Reference yield: 91.0%

methyl-triphenylphosphonium iodide (2065-66-9) + (1S,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)naphthalene-2-one (213026-14-3) → (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene (213026-15-4)

Guidance literature:

methyl-triphenylphosphonium iodide; With sodium hydride; In dimethyl sulfoxide; at 0 - 20 ℃; for 1h;

(1S,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)naphthalene-2-one; In dimethyl sulfoxide; at 75 - 80 ℃; for 24h;

DOI:10.1021/jo9805192

Reference yield:

1,2,4,5-tetramethoxybenzene (2441-46-5) → (1R,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-2-methylene-5-(2-methyl-1,3-dioxolan-2-yl)-naphthalene (213026-15-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 74 percent / HBr; AcOH / 16 h / 20 °C

2.1: Li; NH₃ / tetrahydrofuran; H₂O / 0.75 h / -78 - -33 °C

2.2: 76 percent / tetrahydrofuran; H₂O / 2 h / Heating

3.1: 98 percent / KOtBu / toluene / 4 h / Heating

With potassium tert-butylate; ammonia; hydrogen bromide; lithium; acetic acid; In tetrahydrofuran; water; toluene;

DOI:10.1021/ja011413i

upstream raw materials:

Methyltriphenylphosphonium bromide

(1S,4aS)-trans-decahydro-1-α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,4aβ-dimethyl-5-(2-methyl-1,3-dioxolan-2-yl)naphthalene-2-one

methyl-triphenylphosphonium iodide

(4aS)-1,4aβ-dimethyl-4,4a,7,8-tetrahydronaphthalene-2,5(3H,6H)-dione-5-ethyeneacetal

Downstream raw materials:

(1R,2R,4aS)-trans-decahydro-1α[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2α,4aβ-trimethyl-5-methylene-naphthalene

4,5-Dimethoxy-3-((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylene-decahydro-naphthalen-1-ylmethyl)-[1,2]benzoquinone

(1R,2R,4aS)-trans-decahydro-1α-[(2,3,5,6-tetramethoxyphenyl)methyl]-1β,2α,4aβ,5-tetramethyl-naphthalene

4,5-Dimethoxy-3-((1R,2S,4aS,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ylmethyl)-[1,2]benzoquinone