Fmoc-D-Ser-OH

Base Information

• Chemical Name: Fmoc-D-Ser-OH
• CAS No.: 116861-26-8
• Molecular Formula: C₁₈H₁₇NO₅
• Molecular Weight: 327.337
• Hs Code.: 29242990
• European Community (EC) Number: 695-150-2
• DSSTox Substance ID: DTXSID20350933
• Nikkaji Number: J1.409.562D
• Wikidata: Q72478742
• Mol file: 116861-26-8.mol

Synonyms:Fmoc-D-Ser-OH;116861-26-8;Fmoc-D-serine;D-Serine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropanoic acid;(((9H-Fluoren-9-yl)methoxy)carbonyl)-D-serine;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-serine;N-Fmoc-D-serine;MFCD00077068;N-Fmoc-D-Ala(OH);SCHEMBL1486216;DTXSID20350933;JZTKZVJMSCONAK-MRXNPFEDSA-N;Fmoc-D-Ser-OH, >=98.0%;AKOS016842935;AC-8600;AM82211;CS-W014509;HY-W013793;DS-15006;PD196927;F0607;EN300-81376;A22818;J-300237;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-SERINE;(2R)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-hydroxypropanoic acid;(R)-2-(((9H-FLUOREN-9-YL)METHOXY)CARBONYLAMINO)-3-HYDROXYPROPANOIC ACID;Fmoc-D-Serine;N-alpha-Fmoc-D-Serine;N-(9-Fluorenylmethoxycarbonyl)-d-serine;N-Fmoc-d-serine

Chemical Property of Fmoc-D-Ser-OH

Chemical Property:

• Vapor Pressure: 3.27E-15mmHg at 25°C
• Melting Point: 108-112 °C
• Refractive Index: 11.0 ° (C=1, DMF)
• Boiling Point: 599.3oC at 760 mmHg
• PKA: 3.51±0.10(Predicted)
• Flash Point: 316.2oC
• PSA: 95.86000
• Density: 1.362g/cm3
• LogP: 2.36150
• Storage Temp.: 2-8°C
• XLogP3: 2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 327.11067264
• Heavy Atom Count: 24
• Complexity: 446

Purity/Quality:

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

Fmoc-D-serine 99+% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CO)C(=O)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CO)C(=O)O
• Uses: N-Fmoc-D-serine is an N-Fmoc-protected form of D-Serine (S270975). D-Serine is a neurotransmitter that is concentrated in the mammalian brain, and is one of the very few amino acids that occur in the D- and L-configurations in significant amounts. D-Serine is an potent agonist of the N-methyl-D-aspartate (NMDA) receptor in the brain, which is associated with schizophrenia. Use of D-Serine has been considered as an additional therapy for refractory schizophrenic patients.

Technology Process of Fmoc-D-Ser-OH

There total 4 articles about Fmoc-D-Ser-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: 95.0%

D-Serine (312-84-5,83245-15-2) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (R)-N-(fluoren-9-ylmethoxycarbonyl)serine (73724-45-5,136083-72-2,116861-26-8)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water;

DOI:10.1007/s00726-021-02973-1

Reference yield:

N-(9-fluorenylmethoxycarbonyl)-DL-serine (136083-72-2) → (R)-N-(fluoren-9-ylmethoxycarbonyl)serine (73724-45-5,136083-72-2,116861-26-8) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) → (R)-N-(fluoren-9-ylmethoxycarbonyl)serine (73724-45-5,136083-72-2,116861-26-8) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium carbonate / water; 1,4-dioxane / Cooling with ice

1.2: 5 h / 20 °C

2.1: trifluoroacetic acid / isopropyl alcohol; hexane / 25 °C / Resolution of racemate

With sodium carbonate; trifluoroacetic acid; In 1,4-dioxane; hexane; water; isopropyl alcohol;

DOI:10.1002/bkcs.11694

upstream raw materials:

D-Serine

(fluorenylmethoxy)carbonyl chloride

N-(9-fluorenylmethoxycarbonyl)-DL-serine

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

Downstream raw materials:

N-(9-fluorenylmethyloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-D-serine

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropionic acid methyl ester

N-Fmoc-D-serine tetradecylamide

Refernces

• 1、 Zhu, Lunan,Zhu, Junchen,Sun, Xiaotong,Wu, Yaling,Wang, Huiying,Cheng, Lingping,Shen, Jiawei,Ke, Yanxiong. "Novel chiral stationary phases based on 3,5-dimethyl phenylcarbamoylated β-cyclodextrin combining cinchona alkaloid moiety". . p. 1080 - 1090. Retrieved 2020/05/25.
• 2、 Kuroda, Chiaki,Ochi, Atsushi,Nakane, Noritoshi,Umeyama, Takashi,Muto, Nobuko,Niimura, Nami,Teramoto, Yoshiki,Nogami, Hiroyuki,Reddy, Guvvala N.. "Synthesis of a chiral precursor for no-carrier-added (NCA) PET tracer 6- [18F]fluoro-L-dopa based on regio- and enantioselective alkylation of 2,4- bis(chloromethyl)-5-iodoanisole". . p. 417 - 422. Retrieved 2007/10/03.