90071-62-8

Basic information

• Product Name: H-D-PRO-OTBU
• Synonyms: D-PROLINE, 1,1-DIMETHYLETHYL ESTER;D-PROLINE-OTBU;D-PROLINE T-BUTYL ESTER;D-PROLINE T-BUTYL ESTER HYDROCHLORIDE;D-PYRROLIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER;D-PYRROLIDINE-2-CARBOXYLIC ACID T-BUTYL ESTER HYDROCHLORIDE;H-D-PRO-OTBU;H-D-PRO-OTBU HCL
• CAS NO: 90071-62-8
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• Product Categories: Amino Acids and Derivatives;Amino ester;Amino Acid Derivatives
• Mol File: 90071-62-8.mol

Chemical Properties

• Boiling Point: 219.2 °C at 760 mmHg
• Flash Point: 86.4 °C
• Appearance: /
• Density: 0.995g/cm³
• Vapor Pressure: 0.121mmHg at 25°C
• Refractive Index: 1.454
• Storage Temp.: -15°C
• PKA: 8.32±0.10(Predicted)
• CAS DataBase Reference: H-D-PRO-OTBU(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-PRO-OTBU(90071-62-8)
• EPA Substance Registry System: H-D-PRO-OTBU(90071-62-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-37/38-41-51
• Safety Statements: 26-39
• Hazardous Substances Data: 90071-62-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-D-PRO-OTBU is used as a key intermediate in the synthesis of various pharmaceutical compounds for their therapeutic applications. It plays a crucial role in the production of (R)-(+)-N-Boc-Pipecolic Acid, (S)-(-)-Coniine, (S)-(+)-Pelletierine, (+)-.beta.-Conhydrine, and (S)-(-)-Ropivacaine. These compounds have diverse applications in medicine, such as pain management, muscle relaxation, and treatment of neurological disorders.
Additionally, H-D-PRO-OTBU is used in the formal synthesis of (-)-Lasubine II and (+)-Cermizine C, which are complex organic molecules with potential pharmaceutical applications. The tert-butyl ester group in H-D-PRO-OTBU allows for selective protection and deprotection during the synthesis process, making it an essential component in the development of these complex molecules.

InChI:InChI=1/C9H17NO2/c1-9(2,3)12-8(11)7-5-4-6-10-7/h7,10H,4-6H2,1-3H3/t7-/m1/s1

Upstream product

• 344-25-2 D-Prolin 
• 201206-00-0 Z-D-Pro-OtBu 
• 1416352-40-3 (R)-tert-butyl 4-(1,3-dioxolan-2-yl)-2-(diphenylmethyleneamino)butanoate 

Downstream Products

• 288074-31-7 (R)-1-[(2S,3S)-3-Methyl-2-(2-nitro-benzenesulfonylamino)-pentanoyl]-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 617721-55-8 1-[2,4-dimethyl-3-(2-methyl-quinolin-8-yloxymethyl)-phenyl]-pyrrolidine-2-(R)-carboxylic acid tert-butyl ester 
• 162757-06-4 Z-L-Phe-D-Pro-OtBu 
• 104849-05-0 cyclo[2-aminoisobutyryl-(S)-phenylalanyl-(R)-prolyl-(S)-2-aminosuberoyl-] 
• 221186-79-4 (+)-(R)-tert-butyl 1-[(S)-2-amino-3-phenylpropanoyl]pyrrolidine-2-carboxylate 
• 291312-77-1 H-Aib-L-Phe-D-Pro-OtBu 
• 561039-32-5 (R)-1-{(S)-2-[(1-Amino-cyclohexanecarbonyl)-amino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 221186-91-0 Z-Aib-L-Phe-D-Pro-OtBu 
• 561039-31-4 (R)-1-{(S)-2-[(1-Benzyloxycarbonylamino-cyclohexanecarbonyl)-amino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Stereoselective synthesis of cyclic amino acids via asymmetric phase-transfer catalytic alkylation

An asymmetric synthesis of cyclic amino acids having piperidine and azepane core structures was realized starting from readily available glycine and alanine esters by combination of phase-transfer catalyzed asymmetric alkylation and subsequent reductive a

Evaluation of functional groups on amino acids in cyclic tetrapeptides in histone deacetylase inhibition

The naturally occurring cyclic tetrapeptide, chlamydocin, originally isolated from fungus Diheterospora chlamydosphoria, consists of α-aminoisobutyric acid, l-phenylalanine, d-proline and an unusual amino acid (S)-2-amino-8-((S)-oxiran-2-yl)-8-oxooctanoic acid (Aoe) and inhibits the histone deacetylases (HDACs), a class of regulatory enzymes. The epoxyketone moiety of Aoe is the key functional group for inhibition. The cyclic tetrapeptide scaffold is supposed to play important role for effective binding to the surface of enzymes. In place of the epoxyketone group, hydroxamic acid and sulfhydryl group have been applied to design inhibitor ligands to zinc atom in catalytic site of HDACs. In the research for more potent HDAC inhibitors, we replaced the epoxyketone moiety of Aoe with different functional groups and synthesized a series of chlamydocin analogs as HDAC inhibitors. Among the functional groups, methoxymethylketone moiety showed as potent inhibition as the hydroxamic acid. On the contrary, we confirmed that borate, trifruoromethylketone, and 2-aminoanilide are almost inactive in HDAC inhibition.

D-proline derivatives

New compounds have the formula: wherein R, R1, X and Y have the meanings described herein. Methods are set forth for synthesizing these compounds and using these compounds to treat diseases associated with amyloidosis, such as Alzheimer's disease, maturity onset diabetes mellitus, familial amyloid polyneuropathy, scrapie, and Kreuzfeld-Jacob disease.