130406-31-4

Basic information

• Product Name: (S)-benzyl 2-hydroxy-1-phenylethylcarbamate
• Synonyms: Cbz-(S)-2-phenylglycinol;(S)-benzyl 2-hydroxy-1-phenylethylcarbamate
• CAS NO: 130406-31-4
• Molecular Formula: C₁₆H₁₇NO₃
• Molecular Weight: 271.32
• Mol File: 130406-31-4.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (S)-benzyl 2-hydroxy-1-phenylethylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-benzyl 2-hydroxy-1-phenylethylcarbamate(130406-31-4)
• EPA Substance Registry System: (S)-benzyl 2-hydroxy-1-phenylethylcarbamate(130406-31-4)

Safety Data

• Hazardous Substances Data: 130406-31-4(Hazardous Substances Data)

Usage

Description

(S)-Benzyl 2-hydroxy-1-phenylethylcarbamate, commonly known as (S)-Cetirizine, is a non-sedating antihistamine chemical compound. It is utilized to alleviate the symptoms of allergic conditions such as hay fever and hives. (S)-benzyl 2-hydroxy-1-phenylethylcarbamate operates by blocking the action of histamine, a substance in the body responsible for causing allergic symptoms. (S)-Cetirizine is available in various forms, including tablets, chewable tablets, and syrup, and is typically administered once daily. It is a widely used and well-tolerated medication, with common side effects being drowsiness, dry mouth, and headache.

Uses

Used in Pharmaceutical Industry:
(S)-Benzyl 2-hydroxy-1-phenylethylcarbamate is used as an antihistamine for treating allergic conditions such as hay fever and hives. It functions by blocking the action of histamine, reducing symptoms like sneezing, runny nose, itchy and watery eyes, and itching of the throat or nose. (S)-benzyl 2-hydroxy-1-phenylethylcarbamate is favored for its non-sedating properties, making it suitable for use during daytime hours without causing drowsiness.
Additionally, (S)-Cetirizine is used as an active ingredient in various pharmaceutical formulations, including tablets, chewable tablets, and syrup, to provide relief from allergic symptoms. Its once-daily administration and wide tolerance make it a popular choice for patients seeking relief from allergic reactions.

Upstream product

• 20989-17-7 (2S)-2-phenylglycinol 
• 501-53-1 benzyl chloroformate 
• 100-42-5 styrene 
• 91174-01-5 sodium [(benzyloxy)carbonyl]chloroamide 
• 621-84-1 O-benzyl carbamate 
• 224433-96-9 [(S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-carbamic acid benzyl ester 
• 20989-17-7 Phenylglycinol 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 121411-08-3 (4-Methoxy-phenyl)-[(S)-1-phenyl-2-((R)-toluene-4-sulfinyl)-ethyl]-amine 
• 100-52-7 benzaldehyde 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 224433-92-5 (S)-1-Phenyl-2-((R)-toluene-4-sulfinyl)-ethylamine 
• 2935-35-5 (S)-2-phenylglycine 
• 398125-83-2 C₁₉H₁₉NO₆ 

Downstream Products

• 142873-00-5 Toluene-4-sulfonic acid (S)-2-benzyloxycarbonylamino-2-phenyl-ethyl ester 
• 190393-63-6 (S)-N-(benzyloxycarbonyl)-α-phenylglycinol mesyl ether 
• 5491-18-9 (S)-N-(benzyloxycarbonyl)phenylglycine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 479687-21-3 (S)-2-Oxo-4-phenyl-2λ⁴-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester 
• 479687-25-7 (S)-2,2-Dioxo-4-phenyl-2λ⁶-[1,2,3]oxathiazolidine-3-carboxylic acid benzyl ester 
• 479687-34-8 Benzoic acid (S)-1-((S)-2-amino-2-phenyl-ethyl)-pyrrolidin-3-yl ester 
• 204970-97-8 (2'S,3S)-3-hydroxy-N-{2-[N-methyl-N-4-(N-propylaminocarbonyl)phenyl]amino-2-phenyl}ethylpyrrolidine 
• 479687-32-6 Benzoic acid (S)-1-((S)-2-benzyloxycarbonylamino-2-phenyl-ethyl)-pyrrolidin-3-yl ester 
• 479687-29-1 C₂₇H₂₈N₂O₇S 
• 479687-38-2 Benzoic acid (S)-1-[(S)-2-phenyl-2-(4-propylcarbamoyl-phenylamino)-ethyl]-pyrrolidin-3-yl ester 
• 473916-34-6 (2'S,3S)-3-benzoyloxy-N-{2-[N-methyl-N-4-(N-propylaminocarbonyl)phenyl]amino-2-phenyl}ethylpyrrolidine 
• 62779-70-8 (1S)-1-phenylethylene-1,2-diamine 

Relevant articles and documents

Staudinger/aza-Wittig reaction to access Nβ-protected amino alkyl isothiocyanates

A unified approach to access Nβ-protected amino alkyl isothiocyanates using Nβ-protected amino alkyl azides through a general strategy of Staudinger/aza-Wittig reaction is described. The type of protocol used to access isothiocyanates depends on the availability of precursors and also, especially in the amino acid chemistry, on the behavior of other labile groups towards the reagents used in the protocols; fortunately, we were not concerned about both these factors as precursor-azides were prepared easily by standard protocols, and the present protocol can pave the way for accessing title compounds without affecting Boc, Cbz and Fmoc protecting groups, and benzyl and tertiary butyl groups in the side chains. The present strategy eliminates the need for the use of amines to obtain title compounds and thus, this method is step-economical; additional advantages include retention of chirality, convenient handling and easy purification. A few hitherto unreported compounds were also prepared, and all final compounds were completely characterized by IR, mass, optical rotation, and 1H and 13C NMR studies.

Cinchona alkaloid ester derivatives as ligands in the asymmetric dihydroxylation and aminohydroxylation of alkenes

Cinchona alkaloid ester derivatives were adopted to asymmetric dihydroxylation and asymmetric aminohydroxylation reactions in excellent yields and enantiomeric excesses.

Enantioselective synthesis of cyclic sulfamidates via Pd-catalyzed hydrogenation

Using Pd(CF3;CO2)2/(S,S)-f-binaphane as the catalyst, an efficient enantioselective synthesis of cyclic sulfamidates was developed via asymmetric hydrogenation of the corresponding cyclic imines in 2,2,2-trifluoroethanol at room temperature with high enantioselectivities (up to 99% ee).