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161183-22-8

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161183-22-8 Usage

Description

(3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone is a white solid chemical compound with the molecular formula C15H19NO4. It is a derivative of 2-azetidinone, featuring a four-membered lactam ring, and is commonly used as a reagent in organic synthesis. (3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone is known for its versatility as a building block in the synthesis of various pharmaceutical compounds and its ability to act as a chiral auxiliary in asymmetric synthesis reactions. The presence of the tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom provides stability to the molecule during synthetic processes, making it a valuable component in medicinal chemistry and pharmaceutical development.

Uses

Used in Pharmaceutical Synthesis:
(3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone is used as a building block for the synthesis of various pharmaceutical compounds due to its structural features and reactivity. Its chiral nature allows for the creation of enantiomerically pure products, which is crucial for the development of effective and safe medications.
Used in Asymmetric Synthesis:
In the field of asymmetric synthesis, (3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone is used as a chiral auxiliary to induce selectivity in chemical reactions. This application is vital for producing enantiomerically enriched compounds, which are essential in many biologically active molecules and pharmaceuticals.
Used in Organic Synthesis as a Reagent:
(3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone serves as a versatile reagent in organic synthesis, where its unique structure and functional groups can be utilized in various reaction types, such as nucleophilic additions, cycloadditions, and rearrangements, to construct complex organic molecules.
Used in Medicinal Chemistry Research:
In the realm of medicinal chemistry, (3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone is used as a key intermediate in the development of new drugs and therapeutic agents. Its ability to be modified and functionalized makes it a valuable tool for exploring novel chemical space and discovering potential drug candidates.
Used in the Development of Drug Delivery Systems:
(3R,4S)-1-tert-Butoxycarbonyl-3-acetoxy-4-phenyl-2-azetidinone can be incorporated into drug delivery systems to improve the pharmacokinetics and biodistribution of therapeutic agents. Its chemical properties may allow for the design of prodrugs or drug conjugates that can be activated or released under specific conditions within the body, enhancing the efficacy and safety of treatments.

Check Digit Verification of cas no

The CAS Registry Mumber 161183-22-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,6,1,1,8 and 3 respectively; the second part has 2 digits, 2 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 161183-22:
(8*1)+(7*6)+(6*1)+(5*1)+(4*8)+(3*3)+(2*2)+(1*2)=108
108 % 10 = 8
So 161183-22-8 is a valid CAS Registry Number.
InChI:InChI=1/C16H19NO5/c1-10(18)21-13-12(11-8-6-5-7-9-11)17(14(13)19)15(20)22-16(2,3)4/h5-9,12-13H,1-4H3/t12-,13+/m0/s1

161183-22-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name tert-butyl (3R,4S)-3-acetyloxy-2-oxo-4-phenylazetidine-1-carboxylate

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:161183-22-8 SDS

161183-22-8Synthetic route

C16H19NO5
161183-22-8

C16H19NO5

C38H48O13

C38H48O13

C52H65NO17

C52H65NO17

Conditions
ConditionsYield
Stage #1: C38H48O13 In tetrahydrofuran at -50 - -40℃; for 0.5 - 1h; Alkaline conditions;
Stage #2: C16H19NO5 In trifluoroacetic acid-d1 at 0℃; for 1 - 3h;
C16H19NO5
161183-22-8

C16H19NO5

10-deacetylbaccatin III
32981-86-5

10-deacetylbaccatin III

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

C55H71NO19
1056998-48-1

C55H71NO19

Conditions
ConditionsYield
Stage #1: 10-deacetylbaccatin III; di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; for 0.5 - 2h; Argon atmosphere;
Stage #2: C16H19NO5 In tetrahydrofuran at -50 - 0℃; for 1.5 - 4h;
Stage #1: 10-deacetylbaccatin III; di-tert-butyl dicarbonate In tetrahydrofuran at 20℃; Alkaline conditions; Inert atmosphere;
Stage #2: C16H19NO5 In tetrahydrofuran at -50 - 0℃; Inert atmosphere; Alkaline conditions;

161183-22-8Upstream product

161183-22-8Downstream Products

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