(S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester

Base Information

• Chemical Name: (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester
• CAS No.: 308279-67-6
• Molecular Formula: C₂₄H₃₆N₂O₆
• Molecular Weight: 448.56

Synonyms:(S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester

Chemical Property of (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester

There total 6 articles about (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-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: 97.0%

Boc-L-aIle-OH (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9) + O-benzyl-L-serine allyl ester hydrochloride → (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester (308279-67-6)

Guidance literature:

With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In dichloromethane; at 0 - 20 ℃; for 8.5h;

DOI:10.1021/ja002547j

Reference yield:

D-allo-isoleucine (1509-34-8,959215-79-3,18875-42-8) → (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester (308279-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / aq. NaOH / dioxane / 2.5 h / 20 °C

2: 97 percent / PyBOP; Et₃N / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With sodium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja002547j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-3-Benzyloxy-2-((2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoylamino)-propionic acid allyl ester (308279-67-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / aq. NaOH / dioxane / 2.5 h / 20 °C

2: 97 percent / PyBOP; Et₃N / CH₂Cl₂ / 8.5 h / 0 - 20 °C

With sodium hydroxide; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja002547j

upstream raw materials:

Boc-L-aIle-OH

D-allo-isoleucine

di-tert-butyl dicarbonate

BOC-O-benzyl-L-serine

Downstream raw materials:

L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl

N-((2R,3R)-3-hydroxy-2-methylnonanoyl)-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl

1-N-demethyl-24-O-benzyl-globomycin

(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-{(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoylamino}-4-methyl-pentanoylamino)-3-methyl-pentanoylamino]-propionic acid

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