(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

Base Information

Chemical Name:(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate
CAS No.:287929-78-6
Molecular Formula:C₂₄H₄₃NO₆SSi
Molecular Weight:501.76
Hs Code.:

Synonyms:(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

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Chemical Property of (1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

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Technology Process of (1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

There total 9 articles about (1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate 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: 82.0%

: 124-63-0
methanesulfonyl chloride

: 287929-77-5
(1R,2R)-3-{[(tert-butyl)dimethylsilyl]oxy}-1-{[(tert-butoxy)carbonyl]amino}-1-(2,4,6-trimethylphenyl)propan-2-ol

: 287929-78-6
(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -15 - 20 ℃; for 5h;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

: 487-68-3
mesytaldehyde

: 287929-78-6
(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / CH₂Cl₂ / 24 h / Heating

2: 86 percent / DIBAL-H / diethyl ether; hexane / 5 h / 20 °C

3: 4 Angstroem mol. sieves; titanium tetraisopropoxide; tert-butyl hydroperoxide / (+)-diisopropyl L-tartrate / CH₂Cl₂; 2,2,4-trimethyl-pentane / 8 h / -30 °C

4: 97 percent / LiClO₄ / acetonitrile / 24 h / 65 °C

5: 68 percent / H₂ / 15 percent Pd(OH)2/C / methanol / 48 h / 20 °C / 760 Torr

6: 91 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

7: 82 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 4 A molecular sieve; hydrogen; lithium perchlorate; diisobutylaluminium hydride; triethylamine; palladium dihydroxide; L-(+)-diisopropyl tartrate; In methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Ring cleavage / 5: Hydrogenation / 6: Etherification / 7: Acylation;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 287929-78-6
(1R,2R)-2-{[(tert-butoxy)carbonyl]amino}-1-{{[(tert-butyl)dimethylsilyl]oxy}methyl}-2-(2,4,6-trimethylphenyl)ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1: 62 percent / H₂ / 10 percent Pd/C / ethyl acetate / 1 Torr

2: 91 percent / 1H-imidazole / dimethylformamide / 24 h / 20 °C

3: 82 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / -15 - 20 °C

With 1H-imidazole; dmap; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: Reduction / 2: Etherification / 3: Acylation;
DOI:10.1002/(SICI)1522-2675(20000510)83:5<972::AID-HLCA972>3.0.CO;2-9