Z-L-GLA(OTBU)2-OH

Base Information

• Chemical Name: Z-L-GLA(OTBU)2-OH
• CAS No.: 60686-50-2
• Molecular Formula: C22H31 N O8
• Molecular Weight: 437.49
• Mol file: 60686-50-2.mol

Synonyms:1,1,3-Propanetricarboxylicacid, 3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-bis(1,1-dimethylethyl) ester,(S)-; N-[(Benzoyloxy)carbonyl]-g,g-di-tert-butyl-L-g-carboxyglutamic acid

Chemical Property of Z-L-GLA(OTBU)2-OH

Chemical Property:

• PSA: 128.23000
• LogP: 3.44660
• Storage Temp.: -15°C

Purity/Quality:

98%Min ^*data from raw suppliers

Z-L-Gla(OtBu)2-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Z-L-GLA(OTBU)2-OH

There total 11 articles about Z-L-GLA(OTBU)2-OH 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: 92.0%

(2S)-2-(2-benzyloxycarbonylamino-3-hydroxypropyl)malonic acid di-tert-butyl ester (912354-37-1) → N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid (60686-50-2,60686-52-4)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In phosphate buffer; acetonitrile; at 40 ℃; for 18h; pH=6.7;

DOI:10.1021/jo061037q

Reference yield:

2S-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethylene)-malonic acid di-tert-butyl ester (873310-64-6) → N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid (60686-50-2,60686-52-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / H₂ / Pd/C / methanol

2: 92 percent / BiBr₃ / acetonitrile; H₂O / 8 h / 20 °C

3: 92 percent / TEMPO; NaClO₂; NaClO / acetonitrile; aq. phosphate buffer / 18 h / 40 °C / pH 6.7

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; bismuth(III) bromide; hydrogen; palladium on activated charcoal; In methanol; phosphate buffer; water; acetonitrile;

DOI:10.1021/jo061037q

Reference yield:

(4R)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid benzyl ester (133464-37-6) → N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamic acid (60686-50-2,60686-52-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA; HMPA / tetrahydrofuran / -78 °C

1.2: 80 percent / Ac₂O; DMAP; pyridine

2.1: 90 percent / H₂ / Pd/C / methanol

3.1: 92 percent / BiBr₃ / acetonitrile; H₂O / 8 h / 20 °C

4.1: 92 percent / TEMPO; NaClO₂; NaClO / acetonitrile; aq. phosphate buffer / 18 h / 40 °C / pH 6.7

With N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; bismuth(III) bromide; hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; water; acetonitrile;

DOI:10.1021/jo061037q

upstream raw materials:

Z-DL-Gla(OtBu)2-OH

Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester

(2S)-2-(2-benzyloxycarbonylamino-3-hydroxypropyl)malonic acid di-tert-butyl ester

2S-(3-benzyloxycarbonyl-2,2-dimethyloxazolidin-4-ylmethylene)-malonic acid di-tert-butyl ester

Downstream raw materials:

N-benzyloxycarbonyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-γ-tert-butyl-L-glutamylleucine methyl ester

N-benzyloxycarbonyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-L-serine methyl ester

N-benzyloxycarbonyl-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-L-leucine methyl ester

N-(benzyloxycarbonyl)-γ,γ-di-tert-butyl-L-γ-carboxyglutamyl-L-alanyl-L-leucine benzyl ester