N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane

Base Information

• Chemical Name: N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane
• CAS No.: 1263166-93-3
• Molecular Formula: C₁₇H₂₈N₂O₄
• Molecular Weight: 324.42
• Mol file: 1263166-93-3.mol

Synonyms:

Chemical Property of N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane

Chemical Property:

• Boiling Point: 487.1±30.0 °C(Predicted)
• PKA: 12.05±0.46(Predicted)
• Density: 1.14±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• Solubility.: Soluble in Water, DMSO, DCM, DMF

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-(1R,8S,9S)-Bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl-1,8-diamino-3,6-dioxaoctane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: endo-BCN-PEG2-amine is a heterobifunctional PEG linker containing a BCN and an amine group. The BCN group can react with azide-tagged molecules. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc.
• Uses: Amine functionalized cyclooctyne derivative. Cyclooctynes are useful in strain-promoted copper-free azide-alkyne cycloaddition reactions. This strained cyclooctyne will react with azide functionalized compounds or biomolecules without the need for a copper catalyst to result in a stable triazole linkage.

Technology Process of N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane

There total 2 articles about N-(1R,8S,9s)-Bicyclo[6.1.0]non-4-yn-9-ylMethyloxycarbonyl-1,8-diaMino-3,6-dioxaoctane 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: 83.0%

3,6-dioxa-1,8-diaminooctane (929-59-9,892154-56-2) + (1R,8S,9ξ)-bicyclo[6.1.0]non-4-yn-9-ylmethyl (4-nitrophenyl) carbonate → [(1R,8S,9R)-bicyclo[6.1.0]non-4-yn-9-yl]methyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (1263166-93-3)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/anie.201003761

Reference yield: 68.0%

3,6-dioxa-1,8-diaminooctane (929-59-9,892154-56-2) + ((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate (1352642-02-4,1426827-79-3,1493802-77-9) → [(1R,8S,9R)-bicyclo[6.1.0]non-4-yn-9-yl]methyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (1263166-93-3)

Guidance literature:

In dichloromethane; for 3.16667h;

Reference yield: 84.0%

[(1R,8S,9R)-bicyclo[6.1.0]non-4-yn-9-yl]methyl N-{2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (1263166-93-3) + biotin N-Hydroxysuccinimide ester (35013-72-0) → C27H42N4O6S (1393600-24-2)

Guidance literature:

With triethylamine; In dichloromethane; for 5h;

upstream raw materials:

3,6-dioxa-1,8-diaminooctane

((1R,8S,9s)-bicyclo[6.1.0]non-4-yn-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate

Downstream raw materials:

C₂₇H₄₂N₄O₆S

C₂₆H₃₇N₃O₉

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