(2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

Base Information

Chemical Name:(2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine
CAS No.:380371-21-1
Molecular Formula:C₃₈H₄₃IN₂O₄Si
Molecular Weight:746.76
Hs Code.:

Synonyms:(2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

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Technology Process of (2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

There total 10 articles about (2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine 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: 97.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 647028-90-8
4-Hydroxy-6-[2-((2S,3R)-3-iodomethyl-1-trityl-aziridin-2-yl)-oxazol-5-yl]-hex-2-ynoic acid methyl ester

: 380371-21-1
(2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja030452m

Reference yield:

: 13515-76-9,116457-91-1,4465-44-5
methyl N-trityl-L-serinate

: 380371-21-1
(2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

Guidance literature:: Multi-step reaction with 10 steps

1.1: 99 percent / NaH / dimethylformamide / 1 h / 0 °C

2.1: 95 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

3.1: BH₃ / tetrahydrofuran / 1 h / 20 °C

3.2: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.3: tetrahydrofuran / 1.5 h / -78 °C

4.1: 5.84 g / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

5.1: 93 percent / zirconocene dichloride; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

6.1: 50 percent / I₂; PPh₃

7.1: TBAF / tetrahydrofuran / 2 h / 0 °C

8.1: 1.72 g / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

9.1: LiHMDS; CeCl₃ / tetrahydrofuran / 1 h / -78 °C

9.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

10.1: 97 percent / NEtiPr₂ / CH₂Cl₂ / 1 h / 0 °C

With n-butyllithium; cerium(III) chloride; zirconocene dichloride; borane; tetrabutyl ammonium fluoride; iodine; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: Mitsunobu reaction / 8.1: Dess-Martin oxidation;
DOI:10.1021/ja030452m

Reference yield:

: 647028-80-6
(S)-methyl 3-(allyloxy)-2-(tritylamino)propanoate

: 380371-21-1
(2S,3R)-2-[5-[3-tert-butyldimethylsilyloxy-5-methoxycarbonyl-4-pentynyl]oxazol-2-yl]-3-iodomethyl-1-tritylaziridine

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

2.1: BH₃ / tetrahydrofuran / 1 h / 20 °C

2.2: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.3: tetrahydrofuran / 1.5 h / -78 °C

3.1: 5.84 g / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

4.1: 93 percent / zirconocene dichloride; n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 50 percent / I₂; PPh₃

6.1: TBAF / tetrahydrofuran / 2 h / 0 °C

7.1: 1.72 g / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

8.1: LiHMDS; CeCl₃ / tetrahydrofuran / 1 h / -78 °C

8.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

9.1: 97 percent / NEtiPr₂ / CH₂Cl₂ / 1 h / 0 °C

With n-butyllithium; cerium(III) chloride; zirconocene dichloride; borane; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; toluene; 3.1: Mitsunobu reaction / 7.1: Dess-Martin oxidation;
DOI:10.1021/ja030452m