104227-71-6

Basic information

• Product Name: (S)-3-Boc-Amino-gamma-butyrolactone
• Synonyms: (S)-3-BOC-AMINOTETRAHYDROFURAN-5-ONE;(S)-3-BOC-AMINO-GAMMA-BUTYROLACTONE;(S)-3- BOC-AMINO -γ-BUTYROLACTONE;(S)-3-Boc-AMino-g-butyrolactone;CarbaMic acid, [(3S)-tetrahydro-5-oxo-3-furanyl]-, 1,1-diMethylethyl ester;(S)-3-Boc-AMino-GaMMa-ButyrolaCLone;tert-Butyl [(3S)-5-oxotetrahydrofuran-3-yl]carbamate;(S)-tert-Butyl (5-oxotetrahydrofuran-3-yl)carbaMate
• CAS NO: 104227-71-6
• Molecular Formula: C₉H₁₅NO₄
• Molecular Weight: 201.22
• Product Categories: pharmacetical;Tetrahydrofuran Series
• Mol File: 104227-71-6.mol
• Article Data: 15

Chemical Properties

• Melting Point: 113-114 °C
• Boiling Point: 363.7 °C at 760mmHg
• Flash Point: 173.8 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: 2-8°C
• PKA: 11.08±0.20(Predicted)
• CAS DataBase Reference: (S)-3-Boc-Amino-gamma-butyrolactone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Boc-Amino-gamma-butyrolactone(104227-71-6)
• EPA Substance Registry System: (S)-3-Boc-Amino-gamma-butyrolactone(104227-71-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 104227-71-6(Hazardous Substances Data)

Usage

Uses

(S)-tert-Butyl (5-Oxotetrahydrofuran-3-yl)carbamate is a useful reagent in the study of asymmetric synthesis of protected amino acids consitutnes of cyclomarin A.

InChI:InChI=1/C9H15NO4/c1-9(2,3)14-8(12)10-6-4-7(11)13-5-6/h6H,4-5H2,1-3H3,(H,10,12)/t6-/m0/s1

Upstream product

• 91240-51-6 N-tert-butyloxycarbonylaspartic acid anhydride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 128427-10-1 (S)-2-(tert-butoxycarbonylamino)-1,4-butanediol 
• 383418-08-4 3-tert-butoxycarbonylamino-4-(tert-butyl-dimethyl-silanyloxy)-thiobutyric acid S-ethyl ester 
• 130622-08-1 dimethyl N-tert-butoxycarbonyl-L-aspartate 
• 7536-58-5 BOC-L-aspartic acid 4-benzyl ester 
• 13726-67-5 Boc-Asp-OH 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 651036-12-3 [2-(R)-chloro-1-(2-trimethylsilanyl-ethoxymethoxymethyl)-ethyl]-carbamic acid tert-butyl ester 
• 651035-90-4 (2-(R)-chloro-1-hydroxymethyl-ethyl)-carbamic acid tert-butyl ester 
• 651035-84-6 2-(R)-tert-butoxycarbonylamino-3-chloro-propionic acid methyl ester 
• 651036-65-6 3-(S)-tert-butoxycarbonylamino-4-(2-trimethylsilanyl-ethoxymethoxy)-butyric acid methyl ester 
• 83345-44-2 3-tert-butoxycarbonylamino-4-hydroxy-butyric acid 
• 136703-59-8 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester 

Downstream Products

• 221106-60-1 (S)-3-(tert-butoxycarbonylamino)-4-(tert-butyldimethylsiloxy)butyric acid benzyl ester 
• 834919-03-8 ((3S,4S)-4-Amino-5-oxo-tetrahydro-furan-3-yl)-carbamic acid tert-butyl ester 
• 157823-89-7 [(3S,4R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester 
• 368867-73-6 (αS,4S)-α-benzyl-2-oxo-1,3-oxazolidine-4-acetic acid tert-butyl thioester 
• 83345-44-2 3-tert-butoxycarbonylamino-4-hydroxy-butyric acid 

Relevant articles and documents

Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis

In response to Berke?'s report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on a Zn-catalyzed asymmetric Mannich-type reaction in water was developed. Single crystals of HPA-12 for X-ray crystallographic analysis were obtained from ethyl propionate/n-hexane, and the stereochemistry was definitely determined to be 1R,3S, consistent with Berke?'s revised structure.

CRYSTALLINE FORMS OF A PYRROLIDONE DERIVATIVE USEFUL IN THE TREATMENT OF ALZHEIMER'S DISEASE AND PREPARATION THEREOF

The present invention provides processes to manufacture crystalline N-[(3S)-1-[4-[(3-fluorophenyl)methoxy]phenyl]-5-oxo-pyrrolidin-3-yl]acetamide. Also disclosed are polymorphic forms of said compound as well as compounds useful as intermediates in the methods of the invention.

Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids

Homochiral, highly functionalised organolithium reagents derived from l-serine have been generated and reacted with electrophiles. The novel enantiomerically pure adducts thus obtained were then converted, through β-amino alcohols, into novel non-proteinogenic α-amino acids. The methodology also made available a novel boronic acid which was then employed as a Suzuki cross-coupling partner, elaborating a new pathway to phenylalanine analogues.