(2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH

Base Information

• Chemical Name: (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH
• CAS No.: 540482-00-6
• Molecular Formula: C₃₃H₅₅N₃O₇
• Molecular Weight: 605.816
• Mol file: 540482-00-6.mol

Synonyms:(2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH

Chemical Property of (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH

There total 1 articles about (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH 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: 99.0%

(S)-3-Benzyloxy-2-((2S,3R)-2-{(S)-2-[((2R,3R)-3-hydroxy-2-methyl-nonanoyl)-methyl-amino]-4-methyl-pentanoylamino}-3-methyl-pentanoylamino)-propionic acid allyl ester (308279-71-2) → (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH (540482-00-6)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 20 ℃; for 60h;

DOI:10.1016/S0040-4020(03)00110-8

Reference yield: 97.0%

L-allo-Thr(TBS)-GlyOBn (540482-01-7) + (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH (540482-00-6) → (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)-L-aalo-Thr(TBS)-GlyOBn (540482-02-8)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In tetrahydrofuran; at 0 - 20 ℃; for 18h;

DOI:10.1016/S0040-4020(03)00110-8

Reference yield:

(2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)OH (540482-00-6) → O-benzyl globomycin (308279-80-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / Et₃N; diethylcyanophosphate / tetrahydrofuran / 18 h / 0 - 20 °C

2: 95 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 2 h / 0 °C

3: Et₃N / tetrahydrofuran / 14.5 h / 20 °C

4: 14.8 mg / DMAP / toluene; tetrahydrofuran / 3 h / Heating

5: 96 percent / TBAF; AcOH / tetrahydrofuran / 27 h / 0 - 20 °C

With dmap; lithium hydroxide; diethyl cyanophosphonate; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; methanol; water; toluene;

DOI:10.1016/S0040-4020(03)00110-8

upstream raw materials:

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

Downstream raw materials:

(2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)-L-aalo-Thr(TBS)-GlyOBn

globomycin

O-benzyl globomycin

O'TBS-OBn-globomycin