(2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

Base Information

Chemical Name:(2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine
CAS No.:153277-28-2
Molecular Formula:C₂₉H₅₀N₂O₇Si
Molecular Weight:566.811
Hs Code.:

Synonyms:(2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

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Chemical Property of (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

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Technology Process of (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

There total 19 articles about (2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine 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: 94.0%

: (2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 153277-28-2
(2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

Guidance literature:: With trisylhydrazine; triethylamine; In diethyl ether; at 20 ℃; for 72h;
DOI:10.1016/0040-4039(93)88117-2

Reference yield: 78.0%

: 153277-27-1
(2S,3S)-2-[(E)-(S)-3-Benzyloxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-3-methoxymethoxy-pyrrolidine-1-carboxylic acid tert-butyl ester

: 153277-28-2
(2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

Guidance literature:: With trisylhydrazine; triethylamine; In dichloromethane; at 20 ℃; for 56h;

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 153277-28-2
(2S,3S,3'S)-2-<4'-(tert-Butyldimethylsilyloxy)-3'-(benzyloxycarbonylamino)butyl>-1-(tert-butoxycarbonyl)-3-(methoxymethoxy)pyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 78 percent / DMAP, pyridine / CH₂Cl₂ / 16 h / -18 °C

2: 98 percent / NaH / dimethylformamide / 1.) 10 min, 2.) 20 deg C, 16 h

3: 97 percent / NaBH₄ / methanol / 5 h / 20 °C

4: 92 percent / DMAP, Et₃N / CH₂Cl₂ / 16 h / 20 °C

5: 87 percent / MCPBA / CH₂Cl₂ / 1.) ice-cooling, 0.5 h, 2.) 20 deg C, 2 h

6: 60 percent / BuLi / tetrahydrofuran; hexane / 1.) -78 deg C to 0 deg C, 1 h, 2.) -78 deg C to 0 deg C, 4 h

7: 97 percent / Na, KH₂PO₄ / methanol / 18 h / 0 - 20 °C

8: 78 percent / 2,4,6-triisopropylbenzenesulfonyl hydrazide, Et₃N / CH₂Cl₂ / 56 h / 20 °C

With pyridine; dmap; sodium tetrahydroborate; potassium dihydrogenphosphate; n-butyllithium; sodium amalgam; trisylhydrazine; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;