methyl (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate

Base Information

• Chemical Name: methyl (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate
• CAS No.: 126689-05-2
• Molecular Formula: C₁₁H₁₉BO₄
• Molecular Weight: 226.08
• DSSTox Substance ID: DTXSID70569073
• Nikkaji Number: J396.319E
• Mol file: 126689-05-2.mol

Synonyms:126689-05-2;methyl (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate;trans-2-Methoxycarbonylcyclopropane-boronicacidpinacolester;Methyl trans-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate;AMY1137;DTXSID70569073;Methyl- (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate;Methyltrans-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate;trans-methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate;2713420-31-4;Cyclopropanecarboxylic acid, 2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-, Methyl ester, (1R,2R)-rel-

Chemical Property of methyl (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 226.1376392
• Heavy Atom Count: 16
• Complexity: 297

Purity/Quality:

97% ^*data from raw suppliers

trans-2-Methoxycarbonylcyclopropane-boronicacidpinacolester 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2CC2C(=O)OC
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)[C@@H]2C[C@H]2C(=O)OC

Technology Process of methyl (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate

There total 4 articles about methyl (1R,2R)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane-1-carboxylate 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: 65.0%

→ methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane carboxylate (126689-05-2)

Guidance literature:

Reference yield: 44.0%

methyl cyclopropylcarboxylate (2868-37-3) + bis(pinacol)diborane (73183-34-3) → methyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropane carboxylate (126689-05-2)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 2.9-dimethyl-1,10-phenanthroline; In tetrahydrofuran; at 100 ℃; for 24h;

DOI:10.1021/ja400103p

Reference yield:

methyl cyclopropylcarboxylate (2868-37-3) + bis(pinacol)diborane (73183-34-3) → (trans)-2-methoxycarbonylcyclopropane boronic acid pinacol ester (126689-05-2) + (cis)-2-methoxycarbonylcyclopropane boronic acid pinacol ester (126689-05-2)

Guidance literature:

With 2.9-dimethyl-1,10-phenanthroline; (η⁶-mesitylene)(tris-pinacolboryl)iridium; In tetrahydrofuran; at 90 ℃; for 12h; Overall yield = 76 %Chromat.; diastereoselective reaction; Inert atmosphere; Glovebox;

DOI:10.1021/ja400103p

upstream raw materials:

methyl cyclopropylcarboxylate

bis(pinacol)diborane