(9H-Fluoren-1-yl)methyl [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethyl]carbamate

Base Information

• Chemical Name: (9H-Fluoren-1-yl)methyl [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethyl]carbamate
• CAS No.: 148150-68-9
• Molecular Formula: C23H25 N O6
• Molecular Weight: 411.455
• DSSTox Substance ID: DTXSID90698056
• Mol file: 148150-68-9.mol

Synonyms:DTXSID90698056;(9H-Fluoren-1-yl)methyl [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethyl]carbamate

Chemical Property of (9H-Fluoren-1-yl)methyl [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethyl]carbamate

Chemical Property:

• PSA: 86.25000
• LogP: 3.01400
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 411.16818752
• Heavy Atom Count: 30
• Complexity: 617

Purity/Quality:

1-[N-FLUORENYLMETHOXYCARBONYL-(1S)-1-AMINO-2-HYDROXYETHYL]-4-METHYL-2,6,7-TRIOXABICYCLO-[2.2.2]-OCTANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12COC(OC1)(OC2)C(CO)NC(=O)OCC3=C4CC5=CC=CC=C5C4=CC=C3

Technology Process of (9H-Fluoren-1-yl)methyl [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethyl]carbamate

There total 6 articles about (9H-Fluoren-1-yl)methyl [2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)ethyl]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: 76.0%

N-(9-fluorenylmethyloxycarbonyl)-L-serine 3-methyl-3-(hydroxymethyl)oxetane ester (148150-67-8) → 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-hydroxyethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (148150-68-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 8h; Ambient temperature;

Reference yield:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-hydroxyethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (148150-68-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / NaBr / acetone / 30 h / Heating

2: 1.) Cs₂CO₃ / 1.) H₂O, 20 min, 2.) DMF, room temperature, 24 h

3: 1.) BF₃*Et₂O, 2.) TEA / 1.) CH₂Cl₂, 0 deg C to room temperature, 6 h, 2.) 30 min

With TEA; boron trifluoride diethyl etherate; caesium carbonate; sodium bromide; In acetone;

DOI:10.1021/jo972294l

Reference yield:

N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5) → 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-hydroxyethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (148150-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Cs₂CO₃ / 1.) H₂O, 20 min, 2.) DMF, room temperature, 24 h

2: 1.) BF₃*Et₂O, 2.) TEA / 1.) CH₂Cl₂, 0 deg C to room temperature, 6 h, 2.) 30 min

With TEA; boron trifluoride diethyl etherate; caesium carbonate;

DOI:10.1021/jo972294l

upstream raw materials:

N-(9-fluorenylmethyloxycarbonyl)-L-serine 3-methyl-3-(hydroxymethyl)oxetane ester

3-hydroxymethyl-3-methyloxethane

3-bromomethyl-3-methyloxetane

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

Downstream raw materials:

1-[N-(9-fluorenylmethyloxycarbonyl)-(1S,2R)-1-amino-2-hydroxypropyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

[(1S,2S)-2-Hydroxy-2-(4-methoxy-phenyl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

[(1S,2S)-2-Cyclohexyl-2-hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

[(1S,2R)-2-Cyclohexyl-2-hydroxy-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester