(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

Base Information

Chemical Name:(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide
CAS No.:762267-66-3
Molecular Formula:C₂₆H₃₆N₆O₅S
Molecular Weight:544.675
Hs Code.:

(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

Synonyms:(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

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Chemical Property of (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

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Technology Process of (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

There total 12 articles about (S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide 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: 74.0%

: 762267-59-4
2-[(2S,3S,6S)-2-allyloxy-6-(azidomethyl)-3,6-dihydro-2H-pyran-3-yl]acetic acid

: (S)-2-((S)-2-Amino-3-phenyl-propionylamino)-N-methyl-4-methylsulfanyl-butyramide; compound with trifluoro-acetic acid

: 762267-66-3
(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

Guidance literature:: With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1002/ejoc.200400166

Reference yield:

: 121703-30-8
allyl 4,6-di-O-acetyl-2,3-dideoxy-α/β-D-erythro-hex-2-enopyranoside

: 762267-66-3
(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

Guidance literature:: Multi-step reaction with 11 steps

1: 99 percent / KOH / methanol / 2 h / 20 °C

2: 95 percent / DIAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

3: 99 percent / sodium methoxide / methanol / 2 h

4: 77 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

5: 85 percent / hydroquinone; propionic acid / 20 h / 140 °C

6: 95 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

7: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

8: 76 percent / NaN₃ / dimethylformamide / 60 °C

9: 72 percent / methanol / 3 h / 20 °C

10: 93 percent / LiOH / tetrahydrofuran; H₂O / 3.5 h / 20 °C

11: 74 percent / HOBt; EDC; DMAP / Et₃N / dimethylformamide / 20 °C

With dmap; potassium hydroxide; lithium hydroxide; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium methylate; benzotriazol-1-ol; propionic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; hydroquinone; triphenylphosphine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200400166

Reference yield:

: 2873-29-2
D-glucal triacetate

: 762267-66-3
(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-N-methyl-4-methylsulfanyl-butyramide

Guidance literature:: Multi-step reaction with 12 steps

1: 91 percent / FeCl₃ / acetonitrile / 0.5 h

2: 99 percent / KOH / methanol / 2 h / 20 °C

3: 95 percent / DIAD; Ph₃P / tetrahydrofuran / 2 h / 20 °C

4: 99 percent / sodium methoxide / methanol / 2 h

5: 77 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

6: 85 percent / hydroquinone; propionic acid / 20 h / 140 °C

7: 95 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

8: 98 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

9: 76 percent / NaN₃ / dimethylformamide / 60 °C

10: 72 percent / methanol / 3 h / 20 °C

11: 93 percent / LiOH / tetrahydrofuran; H₂O / 3.5 h / 20 °C

12: 74 percent / HOBt; EDC; DMAP / Et₃N / dimethylformamide / 20 °C

With dmap; potassium hydroxide; lithium hydroxide; sodium azide; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; sodium methylate; iron(III) chloride; benzotriazol-1-ol; propionic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; hydroquinone; triphenylphosphine; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/ejoc.200400166