FMOC-(3S,6S,9R)-2-OXO-3-AMINO-7-THIA-1-AZABICYCLO[4.3.0]NONANE-9-CARBOXYLIC ACID

Base Information

• Chemical Name: FMOC-(3S,6S,9R)-2-OXO-3-AMINO-7-THIA-1-AZABICYCLO[4.3.0]NONANE-9-CARBOXYLIC ACID
• CAS No.: 149563-21-3
• Molecular Formula: C₂₃H₂₂N₂O₅S
• Molecular Weight: 438.504
• Mol file: 149563-21-3.mol

Synonyms:Fmoc-β-turn-dipeptide

Chemical Property of FMOC-(3S,6S,9R)-2-OXO-3-AMINO-7-THIA-1-AZABICYCLO[4.3.0]NONANE-9-CARBOXYLIC ACID

Chemical Property:

• Boiling Point: 737.1±60.0 °C(Predicted)
• PKA: 3.17±0.40(Predicted)
• Density: 1.47±0.1 g/cm3(Predicted)

Purity/Quality:

Fmoc-(3s,6s,9r)-2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Fmoc-(3s,6s,9r)-2-oxo-3-amino-7-thia-1-azabicyclo[4.3.0]nonane-9-carboxylic acid is an intermediate used in the synthesis of cyclic hexapeptides and chimeric peptides as mimics of tendamistat.

Technology Process of FMOC-(3S,6S,9R)-2-OXO-3-AMINO-7-THIA-1-AZABICYCLO[4.3.0]NONANE-9-CARBOXYLIC ACID

There total 17 articles about FMOC-(3S,6S,9R)-2-OXO-3-AMINO-7-THIA-1-AZABICYCLO[4.3.0]NONANE-9-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: 87.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + H-L-BTD-OH hydrobromide → Fmoc-β-turn-dipeptide (149563-21-3)

Guidance literature:

With sodium carbonate; In 1,2-dimethoxyethane; for 3h; Ambient temperature;

DOI:10.1021/ja00102a008

Reference yield: 57.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (3S,6S,9R)-2-oxo-3-amino-7-thia-1-aza-bicyclo[4.3.0]nonane-9-carbocylic acid (104937-58-8) → Fmoc-β-turn-dipeptide (149563-21-3)

Guidance literature:

With triethylamine; In water; acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1021/ja9608757

Reference yield: 40.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + (3S,6S,9R)-2-oxo-3-amino-7-thia-1-aza-bicyclo[4.3.0]nonane-9-carbocylic acid (104937-58-8) → Fmoc-β-turn-dipeptide (149563-21-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(01)90216-9

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

(3S,6S,9R)-2-oxo-3-amino-7-thia-1-aza-bicyclo[4.3.0]nonane-9-carbocylic acid

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S, 6S, 9R)-2-oxo-3-phthalimido-7-thia-1-azabicyclo<4.3.0>nonane-9-carboxylic acid

Downstream raw materials:

(3S,6S,9R,1'R)-3-[9'-fluorenylmethyloxycarbonyl]-9-[(1'-carbamoyl-2'-phenyl)ethyl]carbamoyl-2-oxo-7-thio-1-azabicyclo[4.3.0]nonane

5H-thiazolo[3,2-a]pyridine-3-carboxamide, N-{3-[(bis-{[(1,1-dimethylethoxy)carbonyl]amino}methylene)amino]propyl}-hexahydro-5-oxo-6-{[(phenylmethyl)sulfonyl]amino}-, (3R-(3α,6α,8aα))-(9Cl)

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