N-FMOC-L-THREONINE OBO ESTER

Base Information

• Chemical Name: N-FMOC-L-THREONINE OBO ESTER
• CAS No.: 148150-71-4
• Molecular Formula: C24H27 N O6
• Molecular Weight: 425.481
• Mol file: 148150-71-4.mol

Synonyms:Carbamicacid, [(1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)propyl]-,9H-fluoren-9-ylmethyl ester (9CI); Carbamic acid,[2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)propyl]-,9H-fluoren-9-ylmethyl ester, [R-(R*,S*)]-; 2,6,7-Trioxabicyclo[2.2.2]octane,carbamic acid deriv.

Chemical Property of N-FMOC-L-THREONINE OBO ESTER

Chemical Property:

• PSA: 86.25000
• LogP: 3.40250

Purity/Quality:

N-FMOC-L-THREONINE OBO ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-FMOC-L-THREONINE OBO ESTER

There total 12 articles about N-FMOC-L-THREONINE OBO ESTER 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: 85.0%

(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester (150672-50-7) → 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S,2R)-1-amino-2-hydroxypropyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (148150-71-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(00)79241-0

Reference yield:

(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate (99314-44-0) → 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S,2R)-1-amino-2-hydroxypropyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (148150-71-4)

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,2R)-1-amino-2-hydroxypropyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane (148150-71-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / 1,3-dicyclohexylcarbodiimide (DCC), 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 3 h

2: 76 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h / Ambient temperature

3: oxalyl chloride, DMSO / CH₂Cl₂ / 0.17 h / -78 °C

4: CH₂Cl₂; diethyl ether / 0.12 h / -78 °C

With dmap; oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane;

upstream raw materials:

methylmagnesium bromide

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

(2S,3R)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-butyric acid 3-methyl-oxetan-3-ylmethyl ester

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

Refernces

• 1、 Blaskovich, Mark A.,Lajoie, Gilles A.. "Synthesis of a chiral serine aldehyde equivalent and its conversion to chiral α-Amino acid derivatives". . p. 5021 - 5030. Retrieved 2007/10/02.