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

Base Information

• Chemical Name: (2R,3R)-3-hydroxy-2-methyl-nonanoyl-L-N-methyl-Leu-L-allo-Ile-L-Ser(Bn)-L-aalo-Thr(TBS)-GlyOBn
• CAS No.: 540482-02-8
• Molecular Formula: C₅₂H₈₅N₅O₁₀Si
• Molecular Weight: 968.36
• Mol file: 540482-02-8.mol

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

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

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)-L-aalo-Thr(TBS)-GlyOBn

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

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:

(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)-L-aalo-Thr(TBS)-GlyOBn (540482-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / morpholine / Pd(PPh₃)4 / tetrahydrofuran / 60 h / 20 °C

2: 97 percent / Et₃N; diethylcyanophosphate / tetrahydrofuran / 18 h / 0 - 20 °C

With morpholine; diethyl cyanophosphonate; triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;

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

Reference yield: 95.0%

(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) → [(2S,3S)-2-[(S)-3-Benzyloxy-2-((2S,3R)-2-{(S)-2-[((2R,3R)-3-hydroxy-2-methyl-nonanoyl)-methyl-amino]-4-methyl-pentanoylamino}-3-methyl-pentanoylamino)-propionylamino]-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-acetic acid (540482-22-2)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 2h;

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

upstream raw materials:

L-allo-Thr(TBS)-GlyOBn

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

(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:

[(2S,3S)-2-[(S)-3-Benzyloxy-2-((2S,3R)-2-{(S)-2-[((2R,3R)-3-hydroxy-2-methyl-nonanoyl)-methyl-amino]-4-methyl-pentanoylamino}-3-methyl-pentanoylamino)-propionylamino]-3-(tert-butyl-dimethyl-silanyloxy)-butyrylamino]-acetic acid

globomycin

O-benzyl globomycin

O'TBS-OBn-globomycin