(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

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}-4-methyl-pentanoic acid methyl ester
CAS No.:762267-61-8
Molecular Formula:C₂₇H₃₇N₅O₆
Molecular Weight:527.621
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}-4-methyl-pentanoic acid methyl ester

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

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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}-4-methyl-pentanoic acid methyl ester

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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}-4-methyl-pentanoic acid methyl ester

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}-4-methyl-pentanoic acid methyl 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: 72.0%

: 68835-84-7
L-phenylalanyl-L-leucine methyl ester trifluoroacetate

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

: 762267-61-8
(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

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

: 762267-61-8
(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

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: 72 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

: 762267-61-8
(S)-2-{(S)-2-[2-((2S,3S,6S)-2-Allyloxy-6-azidomethyl-3,6-dihydro-2H-pyran-3-yl)-acetylamino]-3-phenyl-propionylamino}-4-methyl-pentanoic acid methyl ester

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: 72 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