(2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid

Base Information

• Chemical Name: (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid
• CAS No.: 170643-02-4
• Molecular Formula: C23H27 N O5
• Molecular Weight: 397.471
• UNII: DU3YJ8UT7T
• DSSTox Substance ID: DTXSID70449427
• Nikkaji Number: J2.653.870J
• Wikidata: Q72503165
• Mol file: 170643-02-4.mol

Synonyms:170643-02-4;Fmoc-d-allo-thr(tbu)-oh;(2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid;(2R,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoic acid;N-(((9H-fluoren-9-yl)methoxy)carbonyl)-O-(tert-butyl)-D-allothreonine;Nalpha-9-Fluorenylmethoxycarbonyl-O-t-butyl-D-allo-threonine;DU3YJ8UT7T;Fmoc-D-allo-Thr(OtBu)-OH;SCHEMBL119402;DTXSID70449427;LZOLWEQBVPVDPR-JLTOFOAXSA-N;Fmoc-O-tert-butyl-D-allo-threonine;MFCD00077074;N-Fmoc-O-tert-Butyl-D-allothreonine;O-(tert-Butyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-allothreonine;AKOS016842925;HY-W048700;AS-72230;CS-0101013;F20065;A882006;J-010640;O-tert-Butyl-N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-D-allothreonine;(2R,3R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-tert-butoxybutanoic acid;(2R,3R)-3-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)butanoic acid;(2R,3R)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoic acid;D-Allothreonine, O-(1,1-dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-;N-alpha-(9-Fluorenylmethyloxycarbonyl)-O-t-butyl-allo-D-threonine (Fmoc-D-aThr(tBu)-OH);O-(1,1-Dimethylethyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-allothreonine

Chemical Property of (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid

Chemical Property:

• Boiling Point: 581.7±50.0 °C(Predicted)
• PKA: 3.42±0.10(Predicted)
• PSA: 84.86000
• Density: 1.197
• LogP: 4.57280
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 397.18892296
• Heavy Atom Count: 29
• Complexity: 564

Purity/Quality:

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

Fmoc-d-allo-thr(tbu)-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C
• Isomeric SMILES: C[C@H]([C@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C

Technology Process of (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid

There total 10 articles about (2R,3R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid 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: 100.0%

Fmoc?(R)?allo?Thr(tBu)?OH → Nα-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether (170643-02-4,138797-71-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; at 20 ℃;

DOI:10.1007/s00726-018-2677-5

Reference yield: 84.0%

(2R,3R)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 2-oxo-2-phenyl-ethyl ester → Nα-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether (170643-02-4,138797-71-4)

Guidance literature:

With zinc; In acetic acid;

DOI:10.1016/00404-0399(50)0992L-

Reference yield: 49.0%

Fmoc-D-alloThr(But)-OBut → C23H27NO5 + (2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine (130674-54-3) + Nα-(9-Fluorenylmethoxycarbonyl)-D-allothreonine t-butyl ether (170643-02-4,138797-71-4)

Guidance literature:

With perchloric acid; In dichloromethane; water; at 20 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Time;

DOI:10.1016/j.tet.2013.06.027

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(2R,3R)-2-Amino-3-tert-butoxy-butyric acid

(2R,3R)-2-N-(9-fluorenylmethyloxycarbonyl)-D-allothreonine

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

Downstream raw materials:

nobilamide B

C₃₂H₅₀N₆O₉S

Refernces

• 1、 Kikuchi, Mari,Konno, Hiroyuki. "Improved synthesis of d-allothreonine derivatives from l-threonine". . p. 7098 - 7101. Retrieved 2013/07/26.
• 2、 Fischer, Peter M.,Sandosham, Jessie. "Synthesis of Nα-(9-Fluorenylmethoxycarbonyl)-Allothreonine t-Butyl Ether via Threonine Oxazolines". . p. 5409 - 5412. Retrieved 2007/10/02.