(S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester

Base Information

• Chemical Name: (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester
• CAS No.: 888788-12-3
• Molecular Formula: C₄₆H₅₅N₃O₁₄S
• Molecular Weight: 906.02

Synonyms:(S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester

Chemical Property of (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester

There total 7 articles about (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl 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: 90.0%

BOC-glycine (4530-20-5) + C39H44N2O11S → (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester (888788-12-3)

Guidance literature:

With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

Reference yield:

(11B)acetic acid [(2R,3S,4R,5R,6S)-3,4-diacetoxy-6-(2,2,2-trichloroethanimidoyl)oxy-5-(2,2,2-trichloroethoxycarbonylamino)tetrahydropyran-2-yl]methyl ester → (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester (888788-12-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MS (AW-300) / CH₂Cl₂ / 1 h / 20 °C

1.2: TMSOTf / CH₂Cl₂ / 1.5 h / -78 °C

1.3: 4.36 g / Zn; AcOH / 8 h / 20 °C

2.1: 90 percent / HBTU; DIEA / dimethylformamide / 2 h / 20 °C

3.1: piperidine / dimethylformamide / 0.75 h / 20 °C

3.2: 90 percent / HBTU; HOBt; DIEA / dimethylformamide / 2 h / 20 °C

With piperidine; MS (AW-300); O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja061165w

Reference yield:

(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester (888788-08-7) → (S)-2-(2-tert-Butoxycarbonylamino-acetylamino)-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-propionic acid allyl ester (888788-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / HBTU; DIEA / dimethylformamide / 2 h / 20 °C

2.1: piperidine / dimethylformamide / 0.75 h / 20 °C

2.2: 90 percent / HBTU; HOBt; DIEA / dimethylformamide / 2 h / 20 °C

With piperidine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

DOI:10.1021/ja061165w

upstream raw materials:

(S)-3-((2R,3R,4R,5S,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-amino-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester

2-(triphenylmethylthio)ethanoic acid

N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester

N-(9-fluorenylmethoxycarbonyl)-O-(2-(2,2,2-trichloroethyloxycarbonyl)amino-2-deoxy-3,4,6-tri-O-acetoxy-β-D-glucopyranosyl)-L-serine allyl ester

Downstream raw materials:

({(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3-(2-tritylsulfanyl-acetylamino)-tetrahydro-pyran-2-yloxy]-ethylcarbamoyl}-methyl)-carbamic acid tert-butyl ester

C₅₀H₇₅N₁₃O₁₆S

C₅₁H₇₇N₁₃O₁₆S

C₅₃H₈₁N₁₃O₁₆S

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