S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester

Base Information

• Chemical Name: S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester
• CAS No.: 100239-05-2
• Molecular Formula: C₂₄H₂₇N₃O₇S
• Molecular Weight: 501.56
• Mol file: 100239-05-2.mol

Synonyms:S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester

Chemical Property of S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester

There total 7 articles about S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl 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: 66.0%

N-(carbobenzyloxy)-S-phthalimido-L-cysteine methyl ester (100239-02-9) + (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone (80582-04-3) → S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester (100239-05-2)

Guidance literature:

With triethylamine; In benzene; at 25 ℃; for 2.5h;

DOI:10.1021/jo00366a010

Reference yield: 66.0%

N-(carbobenzyloxy)-S-phthalimido-L-cysteine methyl ester (100239-02-9) + (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone (80582-04-3) → phthalimide (136918-14-4,85-41-6) + S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester (100239-05-2)

Guidance literature:

triethylamine; In benzene; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)98680-5

Reference yield:

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate (57224-63-2) → S-<4(S)-methyl-3(S)-((benzyloxy)formamido)-2-oxo-1-azetidinyl>-N-(carboboenzyloxy)-L-cysteine methyl ester (100239-05-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) H₂NOH / 1.) MeOH, 0 deg C, 45 min, 2.) MeOH, 5 min

2: 74 percent / (Ph)3P, diisopropyl azodicarbioxylate / tetrahydrofuran / 3 h / Ambient temperature

3: 75 percent / AcONH₄, TiCl₃ / methanol / 2 h

4: 66 percent / Et₃N / benzene / 2.5 h / 25 °C

With titanium(III) chloride; di-isopropyl azodicarboxylate; ammonium acetate; hydroxylamine; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; benzene;

DOI:10.1021/jo00366a010

upstream raw materials:

N-(carbobenzyloxy)-S-phthalimido-L-cysteine methyl ester

(3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone

N,N'-bis[(phenylmethoxy)carbonyl]-L-cystine 1,1'-dimethyl ester

methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

Refernces

• 1、 Woulfe, Steven R.,Iwagami, Hisao,Miller, Marvin J.. "EFFICIENT N-SULFENYLATION OF 2-AZETIDINONES USING S-SUBSTITUTED THIOPHTHALIMIDES". . p. 3891 - 3894. Retrieved 2007/10/02.