(4S,5S)-2-Butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide

Base Information

• Chemical Name: (4S,5S)-2-Butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide
• CAS No.: 161344-84-9
• Molecular Formula: C12H23BN2O4
• Molecular Weight: 270.13
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID20450583
• Nikkaji Number: J942.358C
• Wikidata: Q82270370
• Mol file: 161344-84-9.mol

Synonyms:161344-84-9;(4S,5S)-2-Butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide;2-Butyl-1,3,2-dioxaborolane-4S,5S-dicarboxylic acid bis(dimethylamide);2-butyl-n,n,n',n'-tetramethyl-1,3,2-dioxaborolane-(4s,5s)-dicarboxamide;(4S,5S)-2-butyl-4-N,4-N,5-N,5-N-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide;Butylboronic acid N,N,N',N'-tetramethyl-D-tartaric acid diamide ester;2-BUTYL-1,3,2-DIOXABOROLANE-4S,5S-DICARBOXYLICACIDBIS(DIMETHYLAMIDE);MFCD05663838;SCHEMBL1187026;DTXSID20450583;AFQWQRBBIZKYTE-UWVGGRQHSA-N;AKOS016016432;1,3,2-Dioxaborolane-4,5-dicarboxamide, 2-butyl-N4,N4,N5,N5-tetramethyl-, (4S,5S)-;AS-73801;CS-0146056;D71521;A883118;J-009817;2-Butyl-1,3,2-dioxaborolane-4S,5S-dicarboxylic acid bis-dimethylamide;Butylboronic acid N,N,N',N'-tetramethyl-D-tartaric acid diamide ester, 97%;(4S)-N,N,N',N'-Tetramethyl-2-butyl-1,3,2-dioxaborolane-4alpha,5beta-dicarboxamide;(4S,5S)-2-Butyl-N,N,N'N'-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide;(4S,5S)-2-Butyl-N~4~,N~4~,N~5~,N~5~-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide;154420-26-5

Chemical Property of (4S,5S)-2-Butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.4780(lit.)
• Boiling Point: 305-306 °C(lit.)
• PKA: -0.81±0.40(Predicted)
• Flash Point: >230 °F
• PSA: 59.08000
• Density: 1.096 g/mL at 25 °C(lit.)
• LogP: 0.23510
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 270.1750874
• Heavy Atom Count: 19
• Complexity: 308

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Butyl-1,3,2-dioxaborolane-4S,5S-dicarboxylicAcidBis(dimethylamide) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)C(=O)N(C)C)C(=O)N(C)C)CCCC
• Isomeric SMILES: B1(O[C@@H]([C@H](O1)C(=O)N(C)C)C(=O)N(C)C)CCCC
• Uses: Butylboronic acid N,N,N′,N′-tetramethyl-D-tartaric acid diamide is a dioxaborolane ligand that can be used to prepare:Enantioenriched spiropentanes via zinc catalyzed cyclopropanation of corresponding hydroxymethylallenes. 1,2,3-trisubstituted cyclopropane derivatives by asymmetric cyclopropanation of allylic alcohols in the presence of zinc reagents. Glycolipids plakosides A, B, and their derivatives by Sharpless asymmetric dihydroxylation and cyclopropanation reaction.

Technology Process of (4S,5S)-2-Butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide

There total 3 articles about (4S,5S)-2-Butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide 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: 97.0%

butylboronic acid (4426-47-5) + (S,S)-(-)-2,3-dihydroxy-N,N,N',N'-tetramethylsuccinamide (63126-52-3) → (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide (161344-84-9)

Guidance literature:

In toluene; for 8h; Dean-Stark; Reflux; Inert atmosphere;

DOI:10.1002/anie.201802962

Reference yield: 93.0%

[(2-)-N,O,O'[2,2'-iminobis[ethanolato]]]-2-butylboron (92527-13-4) + (S,S)-(-)-2,3-dihydroxy-N,N,N',N'-tetramethylsuccinamide (63126-52-3) → (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide (161344-84-9)

Guidance literature:

With sodium chloride; In dichloromethane; (inert atm.);

DOI:10.1021/ja982055v

Reference yield: 93.0%

butylboronic acid (4426-47-5) + (-)-N,N,N′,N′-tetramethyl-D-tartaric acid → (4S,5S)-2-butyl-N4,N4,N5,N5-tetramethyl-1,3,2-dioxaborolane-4,5-dicarboxamide (161344-84-9)

Guidance literature:

In toluene; Reflux; Inert atmosphere; Dean-Stark;

DOI:10.1002/chem.201501877

upstream raw materials:

[^(2-)-N,O,O'[2,2'-iminobis[ethanolato]]]-2-butylboron

(S,S)-(-)-2,3-dihydroxy-N,N,N',N'-tetramethylsuccinamide

butylboronic acid

Downstream raw materials:

tert-butyl 4-{(1R,2S)-2-[(2R)-3-(benzyloxy)-2-hydroxy-propyl]cyclopropyl}piperidine-1-carboxylate

(1S,2R)-1-(tributylstannyl)-2-(hydroxymethyl)cyclopropane

Refernces

• 1、 Frost, James R.,Pearson, Colin M.,Snaddon, Thomas N.,Booth, Richard A.,Turner, Richard M.,Gold, Johan,Shaw, David M.,Gaunt, Matthew J.,Ley, Steven V.. "Callipeltosides A, B and C: Total Syntheses and Structural Confirmation". supporting information. p. 13261 - 13277. Retrieved 2015/09/15.
• 2、 Charette, André B.,Juteau, Hélène,Lebel, Hélène,Molinaro, Carmela. "Enantioselective cyclopropanation of allylic alcohols with dioxaborolane ligands: Scope and synthetic applications". . p. 11943 - 11952. Retrieved 2007/10/03.