(R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

Base Information

• Chemical Name: (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester
• CAS No.: 908008-56-0
• Molecular Formula: C₅₄H₇₁N₇O₉
• Molecular Weight: 962.199

Synonyms:

Chemical Property of (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

There total 10 articles about (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-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:

(R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-Amino-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester + (R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid (442900-69-8,253595-70-9) → (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester (908008-56-0)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200600068

Reference yield:

(2R,6S,1'S)-6-[1-(tert-butoxycarbonylamino)-3'-methylbutyl]tetrahydropyran-2-carboxaldehyde → (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester (908008-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 3.04 g / NaClO₂; NaH₂PO₄*2H₂O; amylene / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

2: 168 mg / EDC; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

3: TFA / CH₂Cl₂ / 1.5 h / 20 °C

4: 71 mg / HOBt; DIEA; EDC / CH₂Cl₂ / 12 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1002/ejoc.200600068

Reference yield:

(4S,5S)-4-(tert-butoxycarbonylamino)-2-methyl-9-decen-5-ol (908008-48-0) → (R)-2-[(S)-2-{[(2R,6S)-6-((S)-1-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-3-methyl-butyl)-tetrahydro-pyran-2-carbonyl]-amino}-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester (908008-56-0)

Guidance literature:

Multi-step reaction with 7 steps

1: mCPBA / CH₂Cl₂ / 12 h / 20 °C

2: 1.1 g / camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

3: oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 0.67 h / -60 - 0 °C

4: 3.04 g / NaClO₂; NaH₂PO₄*2H₂O; amylene / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

5: 168 mg / EDC; HOBt; Et₃N / CH₂Cl₂ / 12 h / 20 °C

6: TFA / CH₂Cl₂ / 1.5 h / 20 °C

7: 71 mg / HOBt; DIEA; EDC / CH₂Cl₂ / 12 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; camphor-10-sulfonic acid; benzotriazol-1-ol; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; water; tert-butyl alcohol; 3: Swern oxidation;

DOI:10.1002/ejoc.200600068

upstream raw materials:

(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid

(4S,5S)-4-(tert-butoxycarbonylamino)-2-methyl-9-decen-5-ol

(2S,6R,1'S)-2-[1-(tert-butoxycarbonylamino)-3'-methylbutyl]-6-(hydroxymethyl)tetrahydropyran

(2R,6S,1'S)-6-[1'-(tert-butoxycarbonylamino)-3'-methylbutyl]tetrahydropyran-2-carboxylic acid

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