Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate

Base Information

• Chemical Name: Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate
• CAS No.: 468060-28-8
• Molecular Formula: C₁₄H₂₆BNO₄
• Molecular Weight: 283.176
• DSSTox Substance ID: DTXSID60697011
• Mol file: 468060-28-8.mol

Synonyms:SCHEMBL15154003;DTXSID60697011;WOLHSJKSGPKMIA-UHFFFAOYSA-N;tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate;SB18330;FT-0726181;tert-Butyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]carbamate

Chemical Property of Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate

Chemical Property:

• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 283.1954885
• Heavy Atom Count: 20
• Complexity: 369

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=CCNC(=O)OC(C)(C)C

Technology Process of Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate

There total 2 articles about Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allylcarbamate 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: 93.0%

N-tert-Butoxycarbonyl-1-amino-3-propyne (92136-39-5) + bis(pinacol)diborane (73183-34-3) → tert-butyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]carbamate (1202794-01-1) + (E)-tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl)carbamate (468060-28-8)

Guidance literature:

With NaOC(CH₃)3; methanol; (1,3-dimesitylimidazolidin-2-yl)copper(I) chloride; In tetrahydrofuran; 5.0 mol% Cu-complex, alkyne, diborane, 5.0 mol% NaOC(CH3)3, 1.1 equiv CH3OH, THF, -50°C, 12 h, N2 atm.; >98:2 molar ratio of isomers;

DOI:10.1021/ja2007643

Reference yield:

N-tert-Butoxycarbonyl-1-amino-3-propyne (92136-39-5) + bis(pinacol)diborane (73183-34-3) → 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-Boc-3-amino-1-propene (468060-28-8) + tert-butyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl]carbamate (1202794-01-1)

Guidance literature:

With CuCl; NaOC(CH₃)3; (O₃SC₆H₄)(((CH₃)2CH)3C₆H₂)(C₆H₅)2C₃H₃N₂; In tetrahydrofuran; treatment of acetylene deriv. with 0.9 equiv. of boron compd. in presence of imidazolium deriv., copper chloride, sodium tert-butoxide and 1 equiv. of methanol in THF at 0°C for 12 h under N2; NMR;

DOI:10.1021/ja9089928

Reference yield: 90.0%

(E)-5-(dimethyl(phenyl)silyl)-2-methylenehex-4-en-1-yl acetate + (E)-tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl)carbamate (468060-28-8) → tert-butyl ((2E,7E)-8-(dimethyl(phenyl)silyl)-5-methylenenona-2,7-dien-1-yl)carbamate

Guidance literature:

With potassium fluoride; dichlorobis(tri(2-furyl)phosphine)palladium(II); In methanol; at 20 ℃; for 4h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201805125

upstream raw materials:

N-tert-Butoxycarbonyl-1-amino-3-propyne

bis(pinacol)diborane

Downstream raw materials:

[3-(9-benzyl-9H-purin-6-yl)-allyl]-carbamic acid tert-butyl ester

[3-(1-trityl-1H-imidazol-4-yl)-allyl]-carbamic acid tert-butyl ester

[3-(6-benzylamino-pyridazin-3-yl)-allyl]-carbamic acid tert-butyl ester

[3-(2-azido-1-trityl-1H-imidazol-4-yl)-allyl]-carbamic acid tert-butyl ester