Fmoc-Threoninol(tBu)

Base Information

• Chemical Name: Fmoc-Threoninol(tBu)
• CAS No.: 438239-28-2
• Molecular Formula: C23H29NO4
• Molecular Weight: 383.48
• DSSTox Substance ID: DTXSID20700696
• Mol file: 438239-28-2.mol

Synonyms:Fmoc-Threoninol(tBu);438239-28-2;9H-fluoren-9-ylmethyl N-[1-hydroxy-3-[(2-methylpropan-2-yl)oxy]butan-2-yl]carbamate;9H-fluoren-9-ylmethyl N-[(2R,3R)-1-hydroxy-3-[(2-methylpropan-2-yl)oxy]butan-2-yl]carbamate;MFCD00235950;Fmoc-D-Threoninol(tBu);DTXSID20700696;AM84652;SY018025;FT-0660782;A826427;(9H-Fluoren-9-yl)methyl (3-tert-butoxy-1-hydroxybutan-2-yl)carbamate;(9H-fluoren-9-yl)methyl N-[3-(tert-butoxy)-1-hydroxybutan-2-yl]carbamate;9H-fluoren-9-ylmethyl N-[2-tert-butoxy-1-(hydroxymethyl)propyl]carbamate

Chemical Property of Fmoc-Threoninol(tBu)

Chemical Property:

• Boiling Point: 576.5±45.0 °C(Predicted)
• PKA: 11.00±0.46(Predicted)
• PSA: 67.79000
• Density: 1.144±0.06 g/cm3(Predicted)
• LogP: 4.48050
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 383.20965841
• Heavy Atom Count: 28
• Complexity: 495

Purity/Quality:

97% ^*data from raw suppliers

FMOC-THR(TBU)-OL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C

Technology Process of Fmoc-Threoninol(tBu)

There total 7 articles about Fmoc-Threoninol(tBu) 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: 98.0%

(25,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid (138797-71-4) → (9H-fluoren-9-yl)methyl ((2R,3S)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate (438239-28-2)

Guidance literature:

(25,3S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -30 ℃; for 0.25h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; water; at -30 - 20 ℃; for 0.75h;

Reference yield: 97.0%

Fmoc-Thr(tBu)-OH (71989-35-0,138797-71-4) → Fmoc-Thr(t-Bu)-ol (189337-28-8,438239-28-2)

Guidance literature:

Fmoc-Thr(tBu)-OH; With 4-methyl-morpholine; isobutyl chloroformate; In 1,2-dimethoxyethane; at -15 ℃;

With sodium tetrahydroborate; water; In 1,2-dimethoxyethane;

DOI:10.1002/anie.200904276

Reference yield: 86.4%

(2R,3R)-2-amino-3-(tert-butoxy)butan-1-ol + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Thr(t-Bu)-ol (189337-28-8,438239-28-2)

Guidance literature:

With sodium carbonate; In water; acetone;

upstream raw materials:

Fmoc-Thr(tBu)-OH

N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester

N-benzyloxycarbonyl-O-t-butyl-L-threonine

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

Downstream raw materials:

C₂₃H₂₇NO₄

{(1R,2R)-1-[[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-(2-cyano-ethoxy)-phosphoryloxymethyl]-2-tert-butoxy-propyl}-carbamic acid 9H-fluoren-9-ylmethyl ester

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