(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

Base Information

Chemical Name:(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate
CAS No.:1434564-56-3
Molecular Formula:C₃₁H₄₃NO₇Si
Molecular Weight:569.77
Hs Code.:

Synonyms:(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

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Chemical Property of (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

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Technology Process of (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

There total 7 articles about (2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate 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:

: 7396-44-3
benzyl diethylphosphonoacetate

: 1434564-56-3
(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

: (2R,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: caesium carbonate / cyclohexane / 65 °C

1.2: 2 h / 65 °C

2.1: hydrogenchloride / acetone; water / 48 h / 20 °C

3.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

3.2: 3.5 h / 20 °C

4.1: chloroform / 1.5 h

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; hydrogenchloride; caesium carbonate; acetic acid; In chloroform; cyclohexane; water; acetone; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Wittig Olefination;
DOI:10.1021/jo400558t

Reference yield:

: 1434564-22-3
(2E)-benzyl 4,4-dimethoxybut-2-enoate

: 1434564-56-3
(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

: (2R,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

Guidance literature:: Multi-step reaction with 3 steps

1.1: hydrogenchloride / acetone; water / 48 h / 20 °C

2.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

2.2: 3.5 h / 20 °C

3.1: chloroform / 1.5 h

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; hydrogenchloride; acetic acid; In chloroform; water; acetone; 3.1: |Wittig Olefination;
DOI:10.1021/jo400558t

Reference yield:

: 162398-42-7
(E)-benzyl 4-oxobut-2-enoate

: 1434564-56-3
(2S,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

: (2R,4E)-1-benzyl-2-[(benzyloxycarbonyl)(tert-butyldimethylsilyloxy)amino]-6-tert-butylhex-4-enedioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid / chloroform / 0.17 h / 20 °C

1.2: 3.5 h / 20 °C

2.1: chloroform / 1.5 h

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid; In chloroform; 2.1: |Wittig Olefination;
DOI:10.1021/jo400558t