(1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

Base Information

Chemical Name:(1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate
CAS No.:874894-79-8
Molecular Formula:C₂₂H₂₅NO₆
Molecular Weight:399.444
Hs Code.:

Synonyms:(1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

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Chemical Property of (1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

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Technology Process of (1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

There total 9 articles about (1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate 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: 74.0%

: 206191-15-3
(S)-benzyl 1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-oxo-2-phenylethylcarbamate

: 874894-79-8
(1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

Guidance literature:: With lithium borohydride; In tetrahydrofuran; methanol; at -78 ℃; for 6h;
DOI:10.1016/j.tetasy.2005.10.029

Reference yield:

: 99314-44-0
(3-methyloxetan-3-yl)methyl 4-methylbenzenesulfonate

: 874894-79-8
(1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) Cs₂CO₃, 2.) NaI / 1.) H₂O, 2.) DMF, room temperature, 48 h

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

3: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) -78 deg C, 30 min; 0 deg C, 10 min

4: diethyl ether / 0.08 h / -78 °C

With oxalyl dichloride; TEA; boron trifluoride diethyl etherate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium iodide; In diethyl ether;
DOI:10.1021/jo972294l

Reference yield:

: 3143-02-0
3-hydroxymethyl-3-methyloxethane

: 874894-79-8
(1S,2S)-benzyl 2-hydroxy-1-(4'-methyl-2',6',7'-trioxabicyclo[2.2.2]-octan-1'-yl)-2-phenylethylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / pyridine / 1.5 h

2: 1.) Cs₂CO₃, 2.) NaI / 1.) H₂O, 2.) DMF, room temperature, 48 h

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

4: 1.) DMSO, (COCl)2, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) -78 deg C, 30 min; 0 deg C, 10 min

5: diethyl ether / 0.08 h / -78 °C

With oxalyl dichloride; TEA; boron trifluoride diethyl etherate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; sodium iodide; In pyridine; diethyl ether;
DOI:10.1021/jo972294l