benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

Base Information

Chemical Name:benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate
CAS No.:1363374-78-0
Molecular Formula:C₂₁H₂₉NO₆Si
Molecular Weight:419.55
Hs Code.:

Synonyms:benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

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Chemical Property of benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

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Technology Process of benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

There total 6 articles about benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-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: 70.0%

: 183671-34-3
1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

: 1066-54-2
trimethylsilylacetylene

: 1363374-78-0
benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

Guidance literature:: trimethylsilylacetylene; With isopropylmagnesium bromide; In 2-methyltetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane; In tetrahydrofuran; 2-methyltetrahydrofuran; at 20 ℃; for 2h;

Reference yield: 70.0%

: 61210-52-4
(trimethylsilyl)ethynylmagnesium bromide

: 183671-34-3
1-[N-(benzyloxycarbonyl)-(1S)-1-amino-2-oxoethyl]-4-methyl-2,6,7-trioxa-bicyclo[2.2.2]octane

: 1363374-78-0
benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

Guidance literature:: In tetrahydrofuran; dichloromethane; at -78 ℃; Inert atmosphere;
DOI:10.1021/jm4007774

Reference yield:

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

: 1363374-78-0
benzyl ((1S,2R)-2-hydroxy-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)-4-(trimethylsilyl)but-3-yn-1-yl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 36 h / 70 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 5 h / 0 - 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: dichloromethane / -78 °C / Inert atmosphere

3.2: 2.08 h / -78 °C / Inert atmosphere

3.3: 0.67 h / -78 - 0 °C

4.1: isopropylmagnesium bromide / 2-methyltetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 20 °C

With boron trifluoride diethyl etherate; isopropylmagnesium bromide; tetra-(n-butyl)ammonium iodide; triethylamine; In 2-methyltetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;