Boc-D-Allylglycine

Base Information

• Chemical Name: Boc-D-Allylglycine
• CAS No.: 170899-08-8
• Molecular Formula: C10H17NO4
• Molecular Weight: 215.249
• Hs Code.: 29224985
• Mol file: 170899-08-8.mol

Synonyms:4-Pentenoicacid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, (R)-;(R)-N-tert-Butoxycarbonyl-2-amino-4-pentenoic acid;(R)-N-BOC-Allylglycine;

Chemical Property of Boc-D-Allylglycine

Chemical Property:

• Appearance/Colour: clear pale yellow viscous liquid
• Vapor Pressure: 2.38E-13mmHg at 25°C
• Melting Point: 256°C (dec.)(lit.)
• Refractive Index: 1.4610 (estimate)
• Boiling Point: 352 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 166.7 °C
• PSA: 75.63000
• Density: 1.1835 (rough estimate)
• LogP: 1.93130
• Storage Temp.: 2-8°C

Purity/Quality:

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

Boc-D-allylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Boc-D-Allylglycine

There total 3 articles about Boc-D-Allylglycine 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: 99.0%

tert-butyl ((R)-1-(((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)-1-oxopent-4-en-2-yl)carbamate (185509-08-4) → (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid (90600-20-7) + N-(tert-butoxycarbonyl)-D-allylglycine (170899-08-8)

Guidance literature:

With sodium hydroxide; In methanol; water; for 3.5h; Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/ja9624073

Reference yield: 95.2%

D-allylglycine (54594-06-8) + di-tert-butyl dicarbonate (24424-99-5) → N-(tert-butoxycarbonyl)-D-allylglycine (170899-08-8)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 18h; Cooling with ice;

DOI:10.1021/acs.jmedchem.6b00309

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (S,S)-pseudoephedrine D-allylglycinamide (170642-23-6) → pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + N-(tert-butoxycarbonyl)-D-allylglycine (170899-08-8)

Guidance literature:

With sodium hydroxide; sodium hydrogencarbonate; Yield given. Multistep reaction; 1.) reflux, 2.) 1.5 h;

DOI:10.1021/ja00137a034

upstream raw materials:

di-tert-butyl dicarbonate

(S,S)-pseudoephedrine D-allylglycinamide

D-allylglycine

tert-butyl ((R)-1-(((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)(methyl)amino)-1-oxopent-4-en-2-yl)carbamate

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[3-((R)-2-tert-butoxycarbonylamino-pent-4-enoyloxy)-propyl] ester 5-(2-trimethylsilanyl-ethyl) ester

(R)-2-tert-Butoxycarbonylamino-pent-4-enoic acid 3-((S)-2-benzyloxycarbonylamino-4-methylsulfanyl-butyryloxy)-propyl ester

3(R)--2-oxoperhydroazepine

Refernces

• 1、 Bremner, John B.,Keller, Paul A.,Pyne, Stephen G.,Boyle, Timothy P.,Brkic, Zinka,David, Dorothy M.,Robertson, Mark,Somphol, Kittiya,Baylis, Dean,Coates, Jonathan A.,Deadman, John,Jeevarajah, Darshini,Rhodes, David I.. "Synthesis and antibacterial studies of binaphthyl-based tripeptoids. Part 1". supporting information; experimental part. p. 2611 - 2620. Retrieved 2010/06/16.
• 2、 Myers, Andrew G.,Gleason, James L.,Yoon, Taeyoung,Kung, Daniel W.. "Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids". . p. 656 - 673. Retrieved 2007/10/03.