Fmoc-Hyp-OH

Base Information

• Chemical Name: Fmoc-Hyp-OH
• CAS No.: 88050-17-3
• Molecular Formula: C20H19NO5
• Molecular Weight: 353.375
• Hs Code.: DERIVATION
• European Community (EC) Number: 836-874-2
• DSSTox Substance ID: DTXSID60373242
• Nikkaji Number: J856.949E
• Wikidata: Q72478496
• Mol file: 88050-17-3.mol

Synonyms:Fmoc-Hyp-OH;88050-17-3;Fmoc-trans-4-hydroxy-L-proline;N-Fmoc-trans-4-hydroxy-L-proline;Fmoc-L-4-hydroxyproline;Fmoc-L-Hyp-OH;(2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;(2S,4R)-1-(9H-fluoren-9-ylmethoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid;trans-N-Fmoc-4-hydroxy-L-proline;MFCD00151929;Fmoc-Hyp;(2S,4R)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-hydroxypyrrolidine-2-carboxylic acid;Fmoc-trans-Hyp-OH;SCHEMBL119261;DTXSID60373242;GOUUPUICWUFXPM-XIKOKIGWSA-N;N-alpha-(9-Fluorenylmethyloxycarbonyl)-trans-L-hydroxyproline;Fmoc-trans-4-hydroxy-(L)-proline;AKOS013155408;AKOS015922830;AM81834;CS-W008205;FD21755;AC-24038;DS-13399;EN300-81273;M03165;EN300-20812961;J-300153;Fmoc-Hyp-OH, >=98.0% (sum of enantiomers, HPLC);Z1160837640;1-(9H-Fluorene-9-ylmethoxycarbonyl)-4beta-hydroxy-L-proline;(4R)-1-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-4-hydroxy-L-proline;(2S, 4R)-1-[(9H-fluoren-9-ylmethoxy) carbonyl]-4-hydroxypyrrolidine-2-carboxylic acid;rac-(2R,4S)-1-{[(9H-fluoren-9-yl)methoxy]carbonyl}-4-hydroxypyrrolidine-2-carboxylic acid

Chemical Property of Fmoc-Hyp-OH

Chemical Property:

• Appearance/Colour: White to off-white crystalline powder
• Vapor Pressure: 4.98E-15mmHg at 25°C
• Melting Point: 189-193 °C
• Refractive Index: 1.658
• Boiling Point: 595.5 °C at 760 mmHg
• PKA: 3.74±0.40(Predicted)
• Flash Point: 314 °C
• PSA: 87.07000
• Density: 1.407 g/cm³
• LogP: 2.39320
• Storage Temp.: 2-8°C
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 353.12632271
• Heavy Atom Count: 26
• Complexity: 530

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-Hyp-OH ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(CN(C1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O
• Isomeric SMILES: C1[C@H](CN([C@@H]1C(=O)O)C(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)O

Technology Process of Fmoc-Hyp-OH

There total 2 articles about Fmoc-Hyp-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:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → N-Fmoc-trans-4-Hydroxy-L-Proline (88050-17-3) + (2S,3S)-(3-hydroxy)pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (296774-32-8)

Guidance literature:

L-proline; With ferrous(II) sulfate heptahydrate; sodium L-ascorbate; α-ketoglutaric acid disodium salt; In aq. phosphate buffer; at 30 ℃; pH=7.5; Enzymatic reaction;

(fluorenylmethoxy)carbonyl chloride; In acetonitrile; at 30 ℃; for 0.166667h; Reagent/catalyst; Temperature; Catalytic behavior;

DOI:10.1021/acs.oprd.1c00405

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (2S,3R,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-3,4-dihydroxypyrrolidine-2-carboxylic acid + N-Fmoc-trans-4-Hydroxy-L-Proline (88050-17-3) + (2S,3S)-(3-hydroxy)pyrrolidine-1,2-dicarboxylic acid 1-(9H-fluoren-9-ylmethyl) ester (296774-32-8)

Guidance literature:

L-proline; With ferrous(II) sulfate heptahydrate; sodium L-ascorbate; α-ketoglutaric acid disodium salt; In aq. phosphate buffer; at 30 ℃; pH=7.5; Enzymatic reaction;

(fluorenylmethoxy)carbonyl chloride; In acetonitrile; at 30 ℃; for 0.166667h; Temperature; Catalytic behavior;

DOI:10.1021/acs.oprd.1c00405

Reference yield: 88.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + N-Fmoc-trans-4-Hydroxy-L-Proline (88050-17-3) → Nα-(fluoren-9-ylmethoxycarbonyl)-L-trans-hydroxyproline pentafluorophenyl ester (147836-79-1)

Guidance literature:

With diisopropyl-carbodiimide; In tetrahydrofuran;

DOI:10.1016/0040-4039(95)01509-G

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-proline

Downstream raw materials:

N-Fmoc-3R-hydroxypyrrolidine-5S-methanol

N^α-(fluoren-9-ylmethoxycarbonyl)-L-trans-hydroxyproline pentafluorophenyl ester

(2S,4R)-2-[(1S,2R)-1-Ethoxycarbonyl-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-propylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

(2S,4R)-1-(9H-fluoren-9-yl)methyl-2-methyl-4-hydroxypyrrolidine-1,2-dicarboxylate

Refernces