benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

Base Information

Chemical Name:benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate
CAS No.:135246-01-4
Molecular Formula:C₃₈H₄₆N₂O₅Si
Molecular Weight:638.879
Hs Code.:

benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

Synonyms:benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

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Chemical Property of benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

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Technology Process of benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

There total 4 articles about benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate 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: 77.0%

: 128466-42-2
benzyl (+)-(R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-3-<(tert-butylthio)carbonyl>-4,5-dihydro-2-vinyl-1H-pyrrole-1-carboxylate

: 63126-47-6
(2S)-2-(methoxymethyl)-1-pyrrolidine

: 135246-01-4
benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

Guidance literature:: With silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In acetonitrile; for 20h; Ambient temperature;
DOI:10.1016/S0040-4020(01)96112-5

Reference yield:

: 15925-47-0
S-tert-butyl acetothioacetate

: 135246-01-4
benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

2: 85 percent / triethylamine, trimethylsilyl triflate / CH₂Cl₂ / 1 h / Ambient temperature

3: 1) methyl iodide, 2) DBU / 1) MeCN, r.t., 1 h, 2) CH₂Cl₂, r.t., 90 min

4: 77 percent / diisopropylethylamine, silver triflate / acetonitrile / 20 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(01)96112-5

Reference yield:

: 128466-38-6
benzyl (R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-3-<(tert-butylthio)carbonyl>-4,5-dihydro-2-methyl-1H-pyrrole-1-carboxylate

: 135246-01-4
benzyl (+)-(2'S,5R)-5-<(tert-butyldiphenylsilyl)oxymethyl>-4,5-dihydro-3-(<(2'-methoxymethyl)pyrrolidin-1'-yl>carbonyl)-2-vinyl-1H-pyrrole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / triethylamine, trimethylsilyl triflate / CH₂Cl₂ / 1 h / Ambient temperature

2: 1) methyl iodide, 2) DBU / 1) MeCN, r.t., 1 h, 2) CH₂Cl₂, r.t., 90 min

3: 77 percent / diisopropylethylamine, silver triflate / acetonitrile / 20 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; silver trifluoromethanesulfonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; methyl iodide; In dichloromethane; acetonitrile;
DOI:10.1016/S0040-4020(01)96112-5