(9H-Fluoren-9-yl)methyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate

Base Information

• Chemical Name: (9H-Fluoren-9-yl)methyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate
• CAS No.: 189337-28-8
• Molecular Formula: C23H29NO4
• Molecular Weight: 383.48
• Hs Code.: 2924297099
• DSSTox Substance ID: DTXSID60456786
• Wikidata: Q72470269
• Mol file: 189337-28-8.mol

Synonyms:189337-28-8;FMOC-THR(TBU)-OL;(9H-Fluoren-9-yl)methyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate;(2R,3R)-2-(Fmoc-amino)-3-tert-butoxy-1-butanol;Fmoc-Threoninol(tBu);9H-fluoren-9-ylmethyl N-[(2R,3R)-1-hydroxy-3-[(2-methylpropan-2-yl)oxy]butan-2-yl]carbamate;Fmoc-L-Threoninol(tBu);MFCD00235950;FMOC-O-TERT-BUTYL-L-THREONINOL;Fmoc-Threoninol(OtBu);fmoc-(2r,3r)-2-amino-3-t-butoxy-1-butanol;DTXSID60456786;(9H-fluoren-9-yl)methyl (2R,3R)-3-tert-butoxy-1-hydroxybutan-2-ylcarbamate;AKOS015840319;AKOS015892818;AC-4560;CS-W011755;AS-19185;A880457;(9H-Fluoren-9-yl)methyl [(2R,3R)-3-tert-butoxy-1-hydroxybutan-2-yl]carbamate;Carbamic acid, N-[(1R,2R)-2-(1,1-dimethylethoxy)-1-(hydroxymethyl)propyl]-, 9H-fluoren-9-ylmethyl ester;Carbamic acid,[(1R,2R)-2-(1,1-dimethylethoxy)-1-(hydroxymethyl)propyl]-,9H-fluoren-9-ylmethyl ester(9ci)

Chemical Property of (9H-Fluoren-9-yl)methyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.563
• Boiling Point: 576.497 °C at 760 mmHg
• PKA: 11.00±0.46(Predicted)
• Flash Point: 302.454 °C
• PSA: 67.79000
• Density: 1.145 g/cm³
• LogP: 4.48050
• Storage Temp.: Store at 0°C
• 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:

98% ^*data from raw suppliers

Fmoc-O-tert-butyl-L-threoninol ^*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
• Isomeric SMILES: C[C@H]([C@@H](CO)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC(C)(C)C

Technology Process of (9H-Fluoren-9-yl)methyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate

There total 4 articles about (9H-Fluoren-9-yl)methyl ((2R,3R)-3-(tert-butoxy)-1-hydroxybutan-2-yl)carbamate 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: 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;

Reference yield:

N-benzyloxycarbonyl-O-tert-butylthreonine methyl ester (52785-41-8) → Fmoc-Thr(t-Bu)-ol (189337-28-8,438239-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium hydroxide / water; acetone / pH 10 - 11

2: 4-methyl-morpholine; sodium tetrahydroborate; chloroformic acid ethyl ester / water; tetrahydrofuran / 0 °C

3: 5%-palladium/activated carbon; hydrogen / methanol

4: sodium carbonate / water; acetone

With 4-methyl-morpholine; sodium tetrahydroborate; 5%-palladium/activated carbon; hydrogen; chloroformic acid ethyl ester; sodium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; 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:

C₆₃H₈₉N₁₃O₁₉S₂

{(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

6-[(2R,3R)-3-tert-Butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butoxy]-tetrahydro-pyran-2-carboxylic acid benzyl ester

Refernces

• 1、 -. "POLYMYXIN-BASED COMPOUNDS USEFUL AS ANTIBACTERIAL AGENTS". Paragraph 0064-0065. . Retrieved 2020/04/30.
• 2、 -. "Synthesis method of Fmoc-O-tert-butyl-L-threoninol". . . Retrieved 2017/07/12.