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

Base Information

• Chemical Name: (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid
• CAS No.: 308279-79-0
• Molecular Formula: C₄₄H₇₃N₅O₁₂
• Molecular Weight: 864.09
• Mol file: 308279-79-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 21 articles about (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-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: 97.0%

(S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid allyl ester (308279-78-9) → (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid (308279-79-0)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 72h;

DOI:10.1021/ja002547j

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid (308279-79-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / aq. NaOH / 2-methyl-propan-2-ol / 2 h / 20 °C

2: 82 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

3: 93 percent / PyBOP; triethylamine / CH₂Cl₂ / 17 h / 0 - 20 °C

4: H₂ / Pd/C / methanol / 1.5 h / 20 °C

5: 96 percent / DMAP; DIC; CSA / CH₂Cl₂ / 44 h / 0 - 20 °C

6: 99 percent / TBAF; AcOH / tetrahydrofuran / 22 h / 0 - 20 °C

7: 97 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 72 h / 20 °C

With morpholine; dmap; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; acetic acid; dacarbazine; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja002547j

Reference yield:

N-tert-butoxycarbonyl-L-allo-threonine (2592-18-9,23082-29-3,55674-67-4,85979-33-5,86748-77-8,23082-30-6) → (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-nonanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid (308279-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / triethylamine / CH₂Cl₂ / 2 h / 20 °C

2: 93 percent / PyBOP; triethylamine / CH₂Cl₂ / 17 h / 0 - 20 °C

3: H₂ / Pd/C / methanol / 1.5 h / 20 °C

4: 96 percent / DMAP; DIC; CSA / CH₂Cl₂ / 44 h / 0 - 20 °C

5: 99 percent / TBAF; AcOH / tetrahydrofuran / 22 h / 0 - 20 °C

6: 97 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 72 h / 20 °C

With morpholine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; hydrogen; acetic acid; dacarbazine; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja002547j

upstream raw materials:

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

heptanal

D-allo-isoleucine

di-tert-butyl dicarbonate

Downstream raw materials:

O-benzyl globomycin

globomycin