tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

Base Information

• Chemical Name: tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate
• CAS No.: 175885-18-4
• Molecular Formula: C₂₁H₃₈N₄O₆S
• Molecular Weight: 474.622
• Mol file: 175885-18-4.mol

Synonyms:

Chemical Property of tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

Chemical Property:

Purity/Quality:

99.3% ^*data from raw suppliers

Biotin-PEG2-NH-Boc 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Biotin-PEG2-NH-Boc is a PEG linker with biotin and Boc protected amine moieties. The biotin group is used for the conjugation of proteins and can also be used for labeling. Boc can be removed under acidic condition.

Technology Process of tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate

There total 11 articles about tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate 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: 100.0%

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) + biotin (58-85-5,22879-79-4) → tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate (175885-18-4)

Guidance literature:

With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1021/ja026917a

Reference yield: 87.0%

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) + biotin 2,3,5,6-tetrafluorophenyl ester (173341-32-7) → tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate (175885-18-4)

Guidance literature:

In acetonitrile; at 20 ℃; for 8h;

Reference yield: 86.0%

biotin N-Hydroxysuccinimide ester (35013-72-0) + tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate (153086-78-3) → tert-butyl-N-(2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno(3,4-d)imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethyl)carbamate (175885-18-4)

Guidance literature:

With triethylamine; at 20 ℃; for 16h;

DOI:10.3762/bjoc.11.88

upstream raw materials:

biotin N-Hydroxysuccinimide ester

tert-butyl {2-[2-(2-aminoethoxy)ethoxy]ethyl}carbamate

(3aS,4S,6aR)-4-[5-(1H-imidazol-1-yl)-5-oxopentyl]tetrahydro-1H-thieno-[3,4-d]imidazol-2(3H)-one

biotin

Downstream raw materials:

2-(2-(2-(5-(2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl)pentanoylamino)ethoxy)ethoxy)ethylammonium 2,2,2-trifluoroacetate

C₂₁H₃₉N₅O₅S₃

N-4-formylbenzoyl-N'-biotinyl-3,6-dioxaoctane-1,8-diamine

Refernces

• 1、 Schauenburg, Dominik,Osuna Gálvez, Alberto,Bode, Jeffrey W.. "Covalently functionalized amide cross-linked hydrogels from primary amines and polyethylene glycol acyltrifluoroborates (PEG-KATs)". . p. 4775 - 4782. Retrieved 2018.
• 2、 Fung, Yi Man Eva,Huang, Yiran,Li, Xiaoyu,Peng, Jianzhao,Song, Yinan,Xiong, Feng. "Introducing aldehyde functionality to proteins using ligand-directed affinity labeling". supporting information. p. 6134 - 6137. Retrieved 2020/06/10.
• 3、 Uvyn, Annemiek,De Coen, Ruben,De Wever, Olivier,Deswarte, Kim,Lambrecht, Bart N.,De Geest, Bruno G.. "Cell surface clicking of antibody-recruiting polymers to metabolically azide-labeled cancer cells". supporting information. p. 10952 - 10955. Retrieved 2019/09/18.