(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

Base Information

Chemical Name:(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate
CAS No.:904682-25-3
Molecular Formula:C₂₅H₃₅NO₄Si
Molecular Weight:441.643
Hs Code.:

Synonyms:(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

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Chemical Property of (+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

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Technology Process of (+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

There total 5 articles about (+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)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: 87.0%

: 904682-21-9
(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethylcarbamate

: 106-96-7
propargyl bromide

: 904682-25-3
(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; toluene; at 20 ℃;
DOI:10.1002/chem.200600192

Reference yield:

: 620-02-0
5-Methylfurfural

: 904682-25-3
(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: 71 percent / t-BuOK / CH₂Cl₂ / 2 h / 20 °C

2: 98 percent / MandyPhos(OMe); H₂ / [Rh(nbd)2]BF₄ / methanol; toluene / 16.5 h / 20 °C / 3750.38 Torr

3: 81 percent / DIBALH / tetrahydrofuran; hexane / -78 - 20 °C

4: 73 percent / imidazole / dimethylformamide / 20 °C

5: 87 percent / NaH / dimethylformamide; toluene / 20 °C

With 1H-imidazole; potassium tert-butylate; hydrogen; sodium hydride; diisobutylaluminium hydride; di(norbornadiene)rhodium(I) tetrafluoroborate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1002/chem.200600192

Reference yield:

: 226880-80-4
methyl (2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(5-methyl-2-furyl)acrylate

: 904682-25-3
(+)-benzyl (1R)-2-(5-methyl-2-furyl)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)ethyl(prop-2-ynyl)carbamate

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / MandyPhos(OMe); H₂ / [Rh(nbd)2]BF₄ / methanol; toluene / 16.5 h / 20 °C / 3750.38 Torr

2: 81 percent / DIBALH / tetrahydrofuran; hexane / -78 - 20 °C

3: 73 percent / imidazole / dimethylformamide / 20 °C

4: 87 percent / NaH / dimethylformamide; toluene / 20 °C

With 1H-imidazole; hydrogen; sodium hydride; diisobutylaluminium hydride; di(norbornadiene)rhodium(I) tetrafluoroborate; In tetrahydrofuran; methanol; hexane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.200600192