Fmoc-O-benzyl-L-seryl chloride

Base Information

• Chemical Name: Fmoc-O-benzyl-L-seryl chloride
• CAS No.: 157506-72-4
• Molecular Formula: C25H22ClNO4
• Molecular Weight: 435.89900
• DSSTox Substance ID: DTXSID00465296
• Nikkaji Number: J1.896.898C
• Wikidata: Q82291132
• Mol file: 157506-72-4.mol

Synonyms:Fmoc-O-benzyl-L-seryl chloride;157506-72-4;9H-fluoren-9-ylmethyl N-[(2S)-1-chloro-1-oxo-3-phenylmethoxypropan-2-yl]carbamate;(S)-(9H-Fluoren-9-yl)methyl (3-(benzyloxy)-1-chloro-1-oxopropan-2-yl)carbamate;DTXSID00465296;(S)-(9H-fluoren-9-yl)methyl 3-(benzyloxy)-1-chloro-1-oxopropan-2-ylcarbamate;Carbamic acid, N-[(1S)-2-chloro-2-oxo-1-[(phenylmethoxy)methyl]ethyl]-, 9H-fluoren-9-ylmethyl ester

Chemical Property of Fmoc-O-benzyl-L-seryl chloride

Chemical Property:

• PSA: 64.63000
• LogP: 5.26680
• Storage Temp.: Store at 0-5°C
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 9
• Exact Mass: 435.1237359
• Heavy Atom Count: 31
• Complexity: 586

Purity/Quality:

98.5% ^*data from raw suppliers

Fmoc-O-benzyl-L-seryl chloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(=O)Cl)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@@H](C(=O)Cl)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24

Technology Process of Fmoc-O-benzyl-L-seryl chloride

There total 1 articles about Fmoc-O-benzyl-L-seryl chloride 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: 90.8%

O-benzyl-N-Fmoc-L-serine (122889-11-6,83792-48-7) → Fmoc-L-(Bn)Ser-Cl (157506-72-4)

Guidance literature:

With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00369a042

Reference yield: 85.0%

Fmoc-L-(Bn)Ser-Cl (157506-72-4) → (2-benzyloxy-1-hydroxycarbamoyl-ethyl)-carbamic acid 9H-fluoren-9-ylmethyl ester

Guidance literature:

With hydroxylamine hydrochloride; magnesium oxide; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1016/S0040-4039(03)00830-X

Reference yield: 78.0%

N,O-bis(trimethylsilyl)-L-valine (7364-44-5) + Fmoc-L-(Bn)Ser-Cl (157506-72-4) → Fmoc-Ser(OBn)-Val-OH (938464-44-9)

Guidance literature:

Fmoc-L-(Bn)Ser-Cl; With HOBt*DCHA; In tetrahydrofuran;

N,O-bis(trimethylsilyl)-L-valine; In tetrahydrofuran; Further stages.;

DOI:10.1080/00397910802219536

upstream raw materials:

O-benzyl-N-Fmoc-L-serine

Downstream raw materials:

(2S,4S)-3-[(S)-3-Benzyloxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionyl]-2-(4-chloro-3-nitro-phenyl)-6-oxo-hexahydro-pyrimidine-4-carboxylic acid tert-butyl ester

Fmoc-Ser(OBn)-Val-OH

(7S,9aS)-7-benzyloxymethyl-1,7,8,9a-tetrahydro-pyrazino[2,1-c][1,4]oxazine-6,9-dione

C₄₄H₄₁N₅O₆

Refernces