methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

Base Information

Chemical Name:methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate
CAS No.:351356-45-1
Molecular Formula:C₃₀H₄₆N₄O₈
Molecular Weight:590.717
Hs Code.:

Synonyms:methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

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Chemical Property of methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

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Technology Process of methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

There total 8 articles about methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate 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: 96.0%

: 6306-52-1
L-valine methylester hydrochloride

: 351356-50-8
Boc-Ala-Aib-Hyp(Bn)-OH

: 351356-45-1
methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

Guidance literature:: With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 20h;
DOI:10.1002/1522-2675(20010418)84:4<972::AID-HLCA972>3.0.CO;2-M

Reference yield:

: 351356-12-2
methyl (2S,4R)-4-(benzyloxy)-N-(2-methylpropanoyl)prolinate

: 351356-45-1
methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 21 percent / Lawesson reagent / toluene / 0.83 h / 90 - 100 °C

2.1: COCl₂; DMF / CH₂Cl₂; toluene / 2.17 h / 0 °C

2.2: DABCO / tetrahydrofuran / 0.33 h / 20 °C

3.1: NaN₃ / tetrahydrofuran

4.1: 88 percent / CH₂Cl₂ / 20 °C

5.1: 100 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 20 h / 20 °C

6.1: 96 percent / TBTU; EtN(i-Pr)2 / acetonitrile / 20 h / 20 °C

With Lawessons reagent; lithium hydroxide; sodium azide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1522-2675(20010418)84:4<972::AID-HLCA972>3.0.CO;2-M

Reference yield:

: 66831-17-2
(2S,4R)-methyl 4-(benzyloxy)pyrrolidine-2-carboxylate hydrochloride

: 351356-45-1
methyl N-[(tert-butoxy)carbonyl]-(S)-alanyl-dimethylglycyl-(2S,4R)-4-(benzyloxy)prolyl-(S)-valinate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 82 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

2.1: 21 percent / Lawesson reagent / toluene / 0.83 h / 90 - 100 °C

3.1: COCl₂; DMF / CH₂Cl₂; toluene / 2.17 h / 0 °C

3.2: DABCO / tetrahydrofuran / 0.33 h / 20 °C

4.1: NaN₃ / tetrahydrofuran

5.1: 88 percent / CH₂Cl₂ / 20 °C

6.1: 100 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 20 h / 20 °C

7.1: 96 percent / TBTU; EtN(i-Pr)2 / acetonitrile / 20 h / 20 °C

With Lawessons reagent; lithium hydroxide; sodium azide; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile;
DOI:10.1002/1522-2675(20010418)84:4<972::AID-HLCA972>3.0.CO;2-M