(+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

Base Information

Chemical Name:(+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide
CAS No.:83380-12-5
Molecular Formula:C₃₄H₄₆N₆O₆S
Molecular Weight:666.842
Hs Code.:

(+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

Synonyms:

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Chemical Property of (+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

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Technology Process of (+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

There total 8 articles about (+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide 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: 40.0%

: 83380-11-4
glycylglycylphenylalanylmethioninamide hydrochloride

: 83380-12-5,83435-09-0
(-)-(2R,6R,11R)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

Guidance literature:: With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dimethyl sulfoxide; for 24h; Ambient temperature;
DOI:10.1021/jm00354a006

Reference yield: 40.0%

: 83380-11-4
glycylglycylphenylalanylmethioninamide hydrochloride

: 83380-12-5,83435-09-0
(+)-(2S,6S,11S)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

Guidance literature:: With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dimethyl sulfoxide; for 24h; Ambient temperature;
DOI:10.1021/jm00354a006

Reference yield:

: 6234-26-0
glycylglycyl-(L)-phenylalanine

: 83380-12-5,83435-09-0
(-)-(2R,6R,11R)-<(1,2,3,4,5,6-hexahydro-8-hydroxy-3,6,11-trimethyl-2,6-methano-3-benzazocin-4-yl)carbonyl>glycylglycylphenylalanylmethioninamide

Guidance literature:: Multi-step reaction with 4 steps

1: 1N aq. NaOH / tetrahydrofuran / 3 h / Ambient temperature

2: 1.) isobutyl chloroformate, N-methylmorpholine, 2.) Me₃N / 1.) DMF, -20 deg C, 15 min, 2.) DMF, RT, 3 h

3: 93 percent / 15percent ethanolic HCl / methanol / 0.5 h / 0 °C

4: 40 percent / 1-hydroxybenzotriazole, DCC, Et₃N / dimethylsulfoxide / 24 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; sodium hydroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; trimethylamine; isobutyl chloroformate; In tetrahydrofuran; methanol; dimethyl sulfoxide;
DOI:10.1021/jm00354a006