(1R^*,2S^*,5S^*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate

Base Information

• Chemical Name: (1R^*,2S^*,5S^*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate
• CAS No.: 126019-12-3
• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.337
• Mol file: 126019-12-3.mol

Synonyms:(1R^*,2S^*,5S^*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate

Chemical Property of (1R^*,2S^*,5S^*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R^*,2S^*,5S^*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate

There total 3 articles about (1R^*,2S^*,5S^*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate 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:

2-pentenal (1576-86-9,1576-87-0,764-39-6) → (1R*,2S*,5S*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate (126019-12-3)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; copper diacetate; iodine; toluene-4-sulfonic acid; diborane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00295a032

Reference yield:

1-acetoxy-1,3-pentadiene (17616-45-4,28673-89-4,126019-10-1) → (1R*,2S*,5S*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate (126019-12-3)

Guidance literature:

Multi-step reaction with 2 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

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; iodine; diborane; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00295a032

Reference yield:

3-hydroxymethyl-3-methyloxethane (3143-02-0) + (1R*,2S*,5S*)-2-acetoxy-5-methyl-3-cyclohexene-1-carboxylic acid (126019-11-2) → (1R*,2S*,5S*)-(3-methyl-3-oxetanyl)methyl 2-acetoxy-5-methyl-3-cyclohexenecarboxylate (126019-12-3)

Guidance literature:

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; Yield given. Multistep reaction; 1. MeCN, 0 deg C, 20 min 2. MeCN, 23 h, room temperature;

DOI:10.1021/jo00295a032

upstream raw materials:

3-hydroxymethyl-3-methyloxethane

(1R^*,2S^*,5S^*)-2-acetoxy-5-methyl-3-cyclohexene-1-carboxylic acid

2-pentenal

1-acetoxy-1,3-pentadiene

Downstream raw materials:

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

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

(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