1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

Base Information

Chemical Name:1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate
CAS No.:1309675-20-4
Molecular Formula:C₃₅H₅₄ClO₁₁PSi₂
Molecular Weight:773.405
Hs Code.:

1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

Synonyms:1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

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Chemical Property of 1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

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Technology Process of 1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

There total 3 articles about 1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate 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: 71.0%

: 1309675-18-0
1-benzyl 4-ethyl (2S)-2-((tert-butyldimethylsilyl)oxy)-2-((1R,3R)-3-(2-chloroacetoxy)-1-hydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)succinate

: 137348-87-9
Bis(allyloxy)(diethylamino)phosphine

: 1309675-20-4
1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

Guidance literature:: With 1H-tetrazole; tert.-butylhydroperoxide; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol2011192

Reference yield:

: C₂₇H₄₂O₇Si₂

: 1309675-20-4
1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate; diethyl methoxy borane / tetrahydrofuran; methanol / -78 °C / Inert atmosphere

2: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 20 °C / Inert atmosphere

3: 1H-tetrazole; tert.-butylhydroperoxide / acetonitrile / 0 - 20 °C / Inert atmosphere

With 1H-tetrazole; tert.-butylhydroperoxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; diethyl methoxy borane; triphenylphosphine; In tetrahydrofuran; methanol; toluene; acetonitrile; 1: Prasad reduction / 2: Mitsunobu reaction;
DOI:10.1021/ol2011192

Reference yield:

: 1309675-57-7
1-benzyl 4-ethyl (2S)-2-((tert-butyldimethylsilyl)oxy)-2-((1R,3S)-1,3-dihydroxy-5-(trimethylsilyl)pent-4-yn-1-yl)succinate

: 1309675-20-4
1-benzyl 4-ethyl (2S)-2-((1R,3R)-1-((bis(allyloxy)phosphoryl)oxy)-3-(2-chloroacetoxy)-5-(trimethylsilyl)pent-4-yn-1-yl)-2-((tert-butyldimethylsilyl)oxy)succinate

Guidance literature:: Multi-step reaction with 2 steps

1: di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 20 °C / Inert atmosphere

2: 1H-tetrazole; tert.-butylhydroperoxide / acetonitrile / 0 - 20 °C / Inert atmosphere

With 1H-tetrazole; tert.-butylhydroperoxide; di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; acetonitrile; 1: Mitsunobu reaction;
DOI:10.1021/ol2011192