Ethyl 2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)acetate

Base Information

• Chemical Name: Ethyl 2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)acetate
• CAS No.: 78605-23-9
• Molecular Formula: C10H23 N O2 Si2
• Molecular Weight: 245.469
• European Community (EC) Number: 625-072-6
• Nikkaji Number: J364.554A
• Mol file: 78605-23-9.mol

Synonyms:78605-23-9;Ethyl 2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)acetate;SCHEMBL7903187;NTAZFMGCNVXERO-UHFFFAOYSA-N;2,2,5,5-Tetramethyl-1,2,5-azadisiloiidin-1-acetic acid ethyl ester;FT-0711239;Ethyl 2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-acetate, >=98.0%;2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetic acid ethyl ester

Chemical Property of Ethyl 2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)acetate

Chemical Property:

• Vapor Pressure: 0.00274mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 80-82 °C0.25 mm Hg(lit.)
• Flash Point: 181 °F
• PSA: 29.54000
• Density: 0.95 g/mL at 25 °C(lit.)
• LogP: 2.21320
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 245.12673205
• Heavy Atom Count: 15
• Complexity: 238

Purity/Quality:

98% ^*data from raw suppliers

ETHYL 2,2,5,5-TETRAMETHYL-1,2,5-AZADISILOLIDIN-1-ACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CN1[Si](CC[Si]1(C)C)(C)C

Technology Process of Ethyl 2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)acetate

There total 1 articles about Ethyl 2-(2,2,5,5-tetramethyl-1,2,5-azadisilolidin-1-yl)acetate 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: 98.0%

1,2-bis-(chlorodimethylsilyl)ethane (13528-93-3) + GlyOEt*HCl (459-73-4) → ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate (78605-23-9)

Guidance literature:

With triethylamine; In dichloromethane; for 2h;

DOI:10.1002/hlca.19830660329

Reference yield: 89.0%

ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate (78605-23-9) + (R)-N-propylidene-N-(1-phenylethyl)amine → cis 4-ethyl-1-((R)-1-phenylethyl)-3-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)azetidin-2-one

Guidance literature:

With n-butyllithium; diisopropylamine; zinc(II) chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; -78 deg C, 1 h, then -30 deg C, 20 h;

Reference yield:

tert-butyl glyoxylate (7633-32-1) + ethyl 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetate (78605-23-9) → (2R,3R)-2-Amino-3-hydroxy-succinic acid 4-tert-butyl ester 1-ethyl ester (119594-41-1) + (2S,3S)-2-Amino-3-hydroxy-succinic acid 4-tert-butyl ester 1-ethyl ester (119594-41-1) + (2S,3R)-2-Amino-3-hydroxy-succinic acid 4-tert-butyl ester 1-ethyl ester (119594-41-1)

Guidance literature:

Multistep reaction. Title compound not separated from byproducts;

upstream raw materials:

1,2-bis-(chlorodimethylsilyl)ethane

GlyOEt*HCl

Downstream raw materials:

(2R,3R)-2-Amino-3-hydroxy-succinic acid 4-tert-butyl ester 1-ethyl ester

(2S,3S)-2-Amino-3-hydroxy-succinic acid 4-tert-butyl ester 1-ethyl ester

(2S,3R)-2-Amino-3-hydroxy-succinic acid 4-tert-butyl ester 1-ethyl ester

trans-(3S,4S)-1(R)-(α-methylbenzyl)-3-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentyl)-4-<1-(trimethylsilyl)ethynyl>-2-azetidinone

Refernces

STEREOSELECTIVE ONE-POT SYNTHESES OF TRANS-3-AMINO-β-LACTAMS FROM ZINC ENOLATES OF N-PROTECTED α-AMINOACID ESTERS AND IMINES

10.1016/S0040-4039(00)87909-5

The study in the literature presents a new one-pot synthesis method for 3-amino-β-lactams, which are valuable intermediates for producing various β-lactam antibiotics, including penicillins and cephalosporins. The key chemicals involved are zinc enolates derived from N-protected amino acid esters and imines. Specifically, the zinc enolates are prepared in situ from the corresponding lithium enolates via transmetallation with zinc dichloride. These enolates then react with imines to form the desired 3-amino-β-lactams. The study highlights the high yields and trans-stereoselectivity of this synthetic route, which contrasts with reactions involving lithium enolates. The authors also note that the enolates derived from 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane-1-acetic acid ethyl ester (STABASE) are more stable and yield better results than those from N,N-bis(trimethylsilyl)glycine ethyl ester. The study provides detailed procedures and characterizations of the synthesized compounds, and it suggests that the trans-stereoselectivity arises from a rigid cyclic chair-like transition state of the enolate with an E-imine.