Synthesis routes of 1-Azido-3-iodopropane

1-Azido-3-iodopropane

货号 B8455560

分子量: 211.00 g/mol

InChI 键: GTBCENNLSAZFSM-UHFFFAOYSA-N

注意: 仅供研究使用。不适用于人类或兽医用途。

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Patent

US06958325B2

Procedure details

Monoquaternary spermine containing hydrophilic head-group was prepared in a similar way to compound 3. Briefly, TriBoc-Spermine was reacted with excess of 1-azido-3-iodo-propane in the presence of excess TBA. The resulting quaternarized derivative was hydrogenised under (Pd—C) and Boc protecting group were removed using gaseous HCl in dry methanol.

[Compound]

Name

compound 3

Quantity

0 (± 1) mol

Type

reactant

Reaction Step One

Name

TriBoc-Spermine

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

1-azido-3-iodo-propane

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

Pd—C

Quantity

0 (± 1) mol

Type

catalyst

Reaction Step Three

Name

spermine

Identifiers

REACTION_CXSMILES

C([CH:8]([CH2:24][CH2:25][NH:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][CH2:32][CH2:33][CH2:34][NH2:35])[N:9](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)(OC(C)(C)C)=O.N(CCCI)=[N+]=[N-]>[Pd]>[NH2:35][CH2:34][CH2:33][CH2:32][NH:31][CH2:30][CH2:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24][CH2:8][NH2:9]

Inputs

Step One

[Compound]

Name	compound 3
Quantity	0 (± 1) mol
Type	reactant
Smiles

Step Two

Name	TriBoc-Spermine
Quantity	0 (± 1) mol
Type	reactant
Smiles	C(=O)(OC(C)(C)C)C(N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)CCNCCCCNCCCN

Name	1-azido-3-iodo-propane
Quantity	0 (± 1) mol
Type	reactant
Smiles	N(=[N+]=[N-])CCCI

Step Three

Name	Pd—C
Quantity	0 (± 1) mol
Type	catalyst
Smiles	[Pd]

Conditions

Other

Conditions are dynamic	1
Details	See reaction.notes.procedure_details.

Workups

CUSTOM

Type	CUSTOM
Details	were removed

Outcomes

Product

Name	spermine
Type	product
Smiles	NCCCNCCCCNCCCN

Source

Open Reaction Database (ORD)

Description

The Open Reaction Database (ORD) is an open-access schema and infrastructure for structuring and sharing organic reaction data, including a centralized data repository. The ORD schema supports conventional and emerging technologies, from benchtop reactions to automated high-throughput experiments and flow chemistry. Our vision is that a consistent data representation and infrastructure to support data sharing will enable downstream applications that will greatly improve the state of the art with respect to computer-aided synthesis planning, reaction prediction, and other predictive chemistry tasks.