(S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid
• CAS No.: 860795-17-1
• Molecular Formula: C₃₁H₄₀N₂O₈
• Molecular Weight: 568.667
• Mol file: 860795-17-1.mol

Synonyms:(S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid

Chemical Property of (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid

There total 9 articles about (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic 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)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-prop-(Z)-ylideneamino]-propyl}-azetidine-2-carboxylic acid → (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid (860795-17-1)

Guidance literature:

With sodium cyanoborohydride; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.01.030

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid (860795-17-1)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. KOH

2: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 °C

3: acetic acid; dimethylformamide

4: NaBH₃CN / acetic acid; dimethylformamide

With potassium hydroxide; oxalyl dichloride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; In dichloromethane; acetic acid; N,N-dimethyl-formamide; 4: Swern oxidation;

DOI:10.1016/j.tetlet.2005.01.030

Reference yield:

(S)-benzyl-4-oxo-2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate (124994-66-7) → (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid (860795-17-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: acetic acid; dimethylformamide

1.2: 51 percent / NaBH₃CN / dimethylformamide; acetic acid

2.1: 100 percent / TFA / CH₂Cl₂

3.1: acetic acid; dimethylformamide

4.1: NaBH₃CN / acetic acid; dimethylformamide

With sodium cyanoborohydride; trifluoroacetic acid; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2005.01.030

upstream raw materials:

3,4-dihydro-2H-pyran

(S)-benzyl-4-oxo-2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate

(3S)-3-(Tetrahydroxy-2H-2-pyranyloxy)tetrahydro-2-furanone

(S)-4-Oxo-2-(tetrahydro-pyran-2-yloxy)-butyric acid benzyl ester

Downstream raw materials:

2'-deoxymugineic acid

(S)-1-[(S)-3-Benzyloxycarbonyl-3-((S)-3-benzyloxycarbonyl-3-hydroxy-propylamino)-propyl]-azetidine-2-carboxylic acid