706806-59-9

Basic information

• Product Name: BOC-(S)--ALLYL-PRO-OH
• Synonyms: boc-(s)-α-allyl-pro-oh;Boc-(S)-a-allylproline;(S)-2-Allyl-1-Boc-2-pyrrolidinecarboxylic acid, Boc-α-allyl-D-proline;Boc-(S)-α-allylproline;(Tert-Butoxy)Carbonyl (S)-Alpha-Allyl-Pro
• CAS NO: 706806-59-9
• Molecular Formula: C₁₃H₂₁NO₄
• Molecular Weight: 255.312
• Mol File: 706806-59-9.mol

Chemical Properties

• Boiling Point: 364.3°C at 760 mmHg
• Flash Point: 174.1°C
• Appearance: /
• Density: 1.125g/cm³
• Vapor Pressure: 2.67E-06mmHg at 25°C
• Refractive Index: 1.498
• PKA: 4.02±0.20(Predicted)
• CAS DataBase Reference: BOC-(S)--ALLYL-PRO-OH(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-(S)--ALLYL-PRO-OH(706806-59-9)
• EPA Substance Registry System: BOC-(S)--ALLYL-PRO-OH(706806-59-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• F: 1-10
• Hazardous Substances Data: 706806-59-9(Hazardous Substances Data)

Usage

Uses

Boc-(S)-alpha-allylproline

InChI:InChI=1/C13H21NO4/c1-5-7-13(10(15)16)8-6-9-14(13)11(17)18-12(2,3)4/h5H,1,6-9H2,2-4H3,(H,15,16)/t13-/m1/s1

Upstream product

• 86116-73-6 (2S,5S)-5-allyl-2-tert-butyl-1-aza-3-oxabicyclo<3.3.0>octan-4-one 
• 946075-04-3 C₂₀H₃₇NO₄Si 
• 946075-02-1 C₁₉H₃₅NO₄Si 
• 24424-99-5 di-tert-butyl dicarbonate 
• 195833-47-7 (S)-2-Allyl-pyrrolidine-2-carboxylic acid 

Downstream Products

• 797760-59-9 (5S,8RS)-8-hydroxy-6-oxo-7-oxa-1-azaspiro[4.4]nonane-1-carboxylic acid tert-butyl ester 
• 797760-63-5 (2R,5'S)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid 
• 797760-62-4 (2S,5'S)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid 
• 797760-61-3 (2R,5'S)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid methyl ester 
• 797760-60-2 (2S,5'S)-3-[4-(2,6-dichlorobenzyloxy)phenyl]-2-(1-tert-butoxycarbonyl-6-oxo-1,7-diazaspiro[4.4]nonane-7-yl)propanoic acid methyl ester 

Relevant articles and documents

Ester-enolate Claisen rearrangement of proline-containing α-acyloxy-α-vinylsilane. Synthesis of pyrrolidine-fused glutamate analogs

The stereoselective syntheses of pyrrolidine-fused aspartate and glutamate analogs, (S)-α-carboxymethyl-proline 3 and (S)-α-2-carboxyethyl-proline 4, using a chirality-transferring ester-enolate Claisen rearrangement of α-vinyl-α-acyloxysilane having a Boc-Pro as an acyloxy group, are described. The stereochemical outcome of the proline ester-derived ester-enolate Claisen rearrangement is also disclosed.

A formal total synthesis of (-)-cephalotaxine

A formal total synthesis of (-)-cephalotaxine (1) has been achieved. The key step is an intramolecular aldol condensation of the diketone 9, which in turn was obtained in three steps from the azabicyclic compound 6 derived from D-proline according to Seebach's procedure. Treatment of 9 with a catalytic amount of sodium 2-methyl-2-butanolate in benzene at room temperature gave the α,β-unsaturated ketone 8 in 43% yield. Catalytic hydrogenation of 8 followed by reduction of the ketone 22 with sodium borohydride and acetylation of the resulting alcohol 23 gave the acetoxy derivative 24, which, after deprotection, was acylated with (methylthio)acetic acid to give the amide 26. Compound 26 was converted into optically active ketolactam 4 following the synthetic operations developed for the synthesis of the racemic compound.