2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester
CAS No.:906663-45-4
Molecular Formula:C₃₇H₆₀N₄O₇S
Molecular Weight:704.972
Hs Code.:

2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

Synonyms:2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

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Chemical Property of 2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

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Technology Process of 2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

There total 30 articles about 2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester 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: 32.0%

: cis-3-(5-hydroxypent-3-enyl)piperidine-1,2-dicarboxylic acid 1-tert-butyl ester

: 906663-72-7
5-(2-aminopropionylamino)-6-benzylsulfanyl-4-hydroxy-2-methylhexanoic acid butylamide

: 906663-45-4
2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

: 906663-46-5
2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 4h;
DOI:10.1021/jm060154a

Reference yield:

: (2S,3R)-Piperidine-2,3-dicarboxylic acid 2-methyl ester

: 906663-45-4
2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 3.6 g / NaHCO₃ / methanol / 3 h / sonication

2: oxalyl chloride; DMF / toluene / 1 h / 0 °C

3: 0.96 g / NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5: 93 percent / CH₂Cl₂ / 20 °C

6: 98 percent / H₂ / Pd/C / ethyl acetate / 2 h / 2585.74 Torr

7: 93 percent / TBAF; molecular sieves / tetrahydrofuran / 5 h / 0 - 20 °C

8: oxalyl chloride; DMF / toluene / 1 h / 0 °C

9: NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

10: 1.25 g / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

11: 85 percent / CH₂Cl₂ / 20 °C

12: 90 percent / TBAF; molecular sieves / tetrahydrofuran / 5 h / 0 - 20 °C

13: oxalyl chloride; DMF / toluene / 1 h / 0 °C

14: 0.14 g / NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

15: 100 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

16: 32 percent / PyBOP; iPr₂NEt / CH₂Cl₂ / 4 h / 0 - 20 °C

With lithium hydroxide; sodium tetrahydroborate; molecular sieve; oxalyl dichloride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jm060154a

Reference yield:

: cis-3-formylpiperidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 906663-45-4
2-[1-(1-benzylsulfanylmethyl-4-butylcarbamoyl-2-hydroxypentylcarbamoyl)ethylcarbamoyl]-3-(5-hydroxypent-3-enyl)piperidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 93 percent / CH₂Cl₂ / 20 °C

2: 98 percent / H₂ / Pd/C / ethyl acetate / 2 h / 2585.74 Torr

3: 93 percent / TBAF; molecular sieves / tetrahydrofuran / 5 h / 0 - 20 °C

4: oxalyl chloride; DMF / toluene / 1 h / 0 °C

5: NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

6: 1.25 g / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

7: 85 percent / CH₂Cl₂ / 20 °C

8: 90 percent / TBAF; molecular sieves / tetrahydrofuran / 5 h / 0 - 20 °C

9: oxalyl chloride; DMF / toluene / 1 h / 0 °C

10: 0.14 g / NaBH₄ / tetrahydrofuran / 0.5 h / 0 °C

11: 100 percent / aq. LiOH / tetrahydrofuran / 40 h / 20 °C

12: 32 percent / PyBOP; iPr₂NEt / CH₂Cl₂ / 4 h / 0 - 20 °C

With lithium hydroxide; sodium tetrahydroborate; molecular sieve; oxalyl dichloride; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jm060154a