FMOC-SER(BSI)-OH

Base Information

• Chemical Name: FMOC-SER(BSI)-OH
• CAS No.: 146346-81-8
• Molecular Formula: C24H31 N O5 Si
• Molecular Weight: 441.599
• Mol file: 146346-81-8.mol

Synonyms:N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-O-T-BUTYLDIMETHYLSILYL-L-SERINE;FMOC-O-T-BUTYLDIMETHYLSILYL-L-SERINE;FMOC-SER(BSI)-OH;FMOC-SERINE(BSI)-OH;FMOC-SER(TBUME 2SI)-OH;FMOC-SER(TBDMS)-OH

Chemical Property of FMOC-SER(BSI)-OH

Chemical Property:

• Melting Point: 103 °C
• Boiling Point: 571.4±50.0 °C(Predicted)
• PKA: 3.40±0.10(Predicted)
• PSA: 84.86000
• Density: 1.150±0.06 g/cm3(Predicted)
• LogP: 5.39100
• Storage Temp.: -15°C

Purity/Quality:

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

Fmoc-O-tert-butyldimethylsilyl-L-serine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of FMOC-SER(BSI)-OH

There total 11 articles about FMOC-SER(BSI)-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: 71.0%

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoic acid (146346-81-8,201210-25-5)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.0c01544

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoic acid (146346-81-8,201210-25-5)

Guidance literature:

Multi-step reaction with 2 steps

1: N-methylimidazole / dimethylformamide / 18 h / Ambient temperature

2: 10percent aq. citric acid / H₂O / pH 4

With 1-methyl-1H-imidazole; citric acid; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)60836-5

Reference yield:

[(E)-(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allyl]-carbamic acid 9H-fluoren-9-ylmethyl ester → 3-(tert-butyl-dimethyl-silanyloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid (201210-25-5) + (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoic acid (146346-81-8,201210-25-5)

Guidance literature:

[(E)-(R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((1S,2S,5R)-2-isopropyl-5-methyl-cyclohexyl)-allyl]-carbamic acid 9H-fluoren-9-ylmethyl ester; With ozone; In dichloromethane; at -78 ℃; for 0.0833333h;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 19h;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 5h; Title compound not separated from byproducts;

DOI:10.1021/ol052034n

upstream raw materials:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

O-(tert-butyldimethylsilyl)-L-serine

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

tert-butyldimethylsilyl chloride

Refernces

• 1、 Blasco, Pilar,Chen, Delin,Chen, Sheng,Li, Xuechen,Po, Kathy Hiu Laam. "Convergent Synthesis of Calcium-Dependent Antibiotic CDA3a and Analogues with Improved Antibacterial Activity via Late-Stage Serine Ligation". . . Retrieved 2020.
• 2、 Gagnon, David,Lauzon, Sophie,Godbout, Cedrickx,Spino, Claude. "Sterically biased 3,3-sigmatropic rearrangement of azides: Efficient preparation of nonracemic α-amino acids and heterocycles". . p. 4769 - 4771. Retrieved 2007/10/03.