(1R^*,2S^*,5S^*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene

Base Information

• Chemical Name: (1R^*,2S^*,5S^*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene
• CAS No.: 126019-16-7
• Molecular Formula: C₁₃H₂₀O₄
• Molecular Weight: 240.299

Synonyms:(1R^*,2S^*,5S^*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene

Chemical Property of (1R^*,2S^*,5S^*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene

Chemical Property:

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Technology Process of (1R^*,2S^*,5S^*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene

There total 6 articles about (1R^*,2S^*,5S^*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene 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: 90.0%

(1R*,2S*,5S*)-2-acetoxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene (126019-13-4) → (1R*,2S*,5S*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene (126019-16-7)

Guidance literature:

With sodium methylate; In methanol; for 16h; Ambient temperature;

DOI:10.1021/jo00295a032

Reference yield:

2-pentenal (1576-86-9,1576-87-0,764-39-6) → (1R*,2S*,5S*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene (126019-16-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / p-TosOH, Cu(OAc)2 / 0.67 h / Heating

2: 53 percent / diborane, iodine / CH₂Cl₂; tetrahydrofuran

3: 1. (COCl)2, DMF 2. pyridine / 1. MeCN, 0 deg C, 20 min 2. MeCN, 23 h, room temperature

4: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / 0 °C

5: 90 percent / NaOCH₃ / methanol / 16 h / Ambient temperature

With pyridine; oxalyl dichloride; boron trifluoride diethyl etherate; sodium methylate; N,N-dimethyl-formamide; copper diacetate; iodine; toluene-4-sulfonic acid; diborane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00295a032

Reference yield:

1-acetoxy-1,3-pentadiene (17616-45-4,28673-89-4,126019-10-1) → (1R*,2S*,5S*)-2-hydroxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene (126019-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 53 percent / diborane, iodine / CH₂Cl₂; tetrahydrofuran

2: 1. (COCl)2, DMF 2. pyridine / 1. MeCN, 0 deg C, 20 min 2. MeCN, 23 h, room temperature

3: 78 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / 0 °C

4: 90 percent / NaOCH₃ / methanol / 16 h / Ambient temperature

With pyridine; oxalyl dichloride; boron trifluoride diethyl etherate; sodium methylate; N,N-dimethyl-formamide; iodine; diborane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00295a032

upstream raw materials:

(1R^*,2S^*,5S^*)-2-acetoxy-5-methyl-1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-3-cyclohexene

3-hydroxymethyl-3-methyloxethane

2-pentenal

1-acetoxy-1,3-pentadiene

Downstream raw materials:

(1S^*,2R^*,4S^*,5S^*,6R^*)-9(E)-<2-<(tert-butyldiphenylsilyl)oxy>-1-ethylidene>-1,5-dihydroxy-4-methyl-2-(4-methyl-2,6,7-trioxabicyclo<2.2.2>oct-1-yl)-7-oxabicyclo<4.3.0>nonane

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