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

Base Information

• Chemical Name: (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid
• CAS No.: 742063-00-9
• Molecular Formula: C₄₃H₇₁N₅O₁₂
• Molecular Weight: 850.063

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

Chemical Property of (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid

Chemical Property:

Purity/Quality:

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Technology Process of (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid

There total 5 articles about (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid 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:

(S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid allyl ester → (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid (742063-00-9)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/j.bmc.2003.10.055

Reference yield:

3-oxononanoic acid methyl ester (51756-07-1) → (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid (742063-00-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / H₂ / [RuCl₂{(R)-binap}(dmf)n] / methanol / 4 h / 100 °C / 4560 Torr

2: 100 percent / NaOH / methanol; H₂O / 3.5 h / 0 - 20 °C

3: 100 percent / Et₃N; diethylcyanophosphate / tetrahydrofuran / 0 - 20 °C

4: 90 percent / DMAP; CSA; diisopropylcarbodiimide / CH₂Cl₂ / 20 °C

5: TBAF; AcOH / tetrahydrofuran / 18 h / 0 - 20 °C

6: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 18 h / 20 °C

With morpholine; dmap; sodium hydroxide; diethyl cyanophosphonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triethylamine; diisopropyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; [RuCl₂((R)-BINAP)(dmf)n]; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1016/j.bmc.2003.10.055

Reference yield:

N-methyl-L-leucine-L-allo-isoleucine-O-benzyl-L-serine allyl ester (308279-70-1) → (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid (742063-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / Et₃N; diethylcyanophosphate / tetrahydrofuran / 0 - 20 °C

2: 90 percent / DMAP; CSA; diisopropylcarbodiimide / CH₂Cl₂ / 20 °C

3: TBAF; AcOH / tetrahydrofuran / 18 h / 0 - 20 °C

4: morpholine / Pd(PPh₃)4 / tetrahydrofuran / 18 h / 20 °C

With morpholine; dmap; diethyl cyanophosphonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic acid; triethylamine; diisopropyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2003.10.055

upstream raw materials:

3-oxononanoic acid methyl ester

N-methyl-L-leucine-L-allo-isoleucine-O-benzyl-L-serine allyl ester

N-((3R)-3-hydroxynonanoyl)-N-Me-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl

N-((3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-nonanoyl)-N-Me-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl

Downstream raw materials:

3-demethyl-24-O-benzyl-globomycin

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