102988-92-1

Basic information

• Product Name: C₂₇H₃₂N₂O₇
• Synonyms: C₂₇H₃₂N₂O₇
• CAS NO: 102988-92-1
• Molecular Weight: 496.56
• Mol File: 102988-92-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₂₇H₃₂N₂O₇(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₇H₃₂N₂O₇(102988-92-1)
• EPA Substance Registry System: C₂₇H₃₂N₂O₇(102988-92-1)

Safety Data

• Hazardous Substances Data: 102988-92-1(Hazardous Substances Data)

Upstream product

• 7669-64-9 (2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-3-phenylpropanoyl)tetrahydro-1H-pyrrole-2-carboxylic acid 
• 543-27-1 isobutyl chloroformate 
• 2448-45-5 N-(Benzyloxycarbonyl)-D-phenylalanine 
• 63358-25-8 Z-D-Phe-OTCP 
• 17460-56-9 Z-D-Phe-Pro 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 41518-17-6 Z-Phe-O-COO-isoBu 
• 1161-13-3 N-Cbz-L-Phe 
• 28426-51-9 methyl ((benzyloxy)carbonyl)-L-phenylalanyl-L-prolinate 

Downstream Products

• 126644-60-8 N-[3-(5-Benzyl-6-oxo-5,6,8,9,10,10a-hexahydro-imidazo[1,2-a]pyrrolo[2,1-c]pyrazin-2-yl)-propyl]-guanidine 
• 83997-16-4 D-Phe-Pro-Arg-H*H₂SO₄ 
• 77433-27-3 Z-D-Phe-Pro-Arg(Z)-H 
• 184295-93-0 (2S,3S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-3-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-hydroxy-butyric acid methyl ester 
• 184296-04-6 Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr-OMe 
• 184295-97-4 Cbz-D-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr-OMe 
• 184296-05-7 Cbz-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe 
• 184295-98-5 Cbz-D-Val-Ser(TBDMS)-D-Phe-Ser(TBDMS)-Phe-Pro-allo-Thr(oxaz)-OMe 
• 184296-07-9 (5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 
• 184296-10-4 (5S,8S,11R,14S,17S,20S,22aS)-5,11-Dibenzyl-8,14-bis-(tert-butyl-dimethyl-silanyloxymethyl)-20-((S)-1-hydroxy-ethyl)-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone 
• 184296-14-8 (2S,8S,11S,14R,17S,20S,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone 
• 184295-99-6 (2S,8S,11S,14R,17S,20R,23S,24R)-8,14-Dibenzyl-11,17-bis-hydroxymethyl-20-isopropyl-24-methyl-25-oxa-6,9,12,15,18,21,26-heptaaza-tricyclo[21.2.1.0^2,6]hexacos-1⁽²⁶⁾-ene-7,10,13,16,19,22-hexaone 
• 184296-00-2 cyclo[D-Val-Ser(oxaz)-D-Phe-Ser(oxaz)-Phe-Pro-Allo-Thr(oxaz)] 

Relevant articles and documents

Total synthesis and assignment of configuration of lissoclinamide 7

The first total synthesis of lissoclinamide 7, a 21-membered cyclopeptide isolated from Lissoclinum bistratum, was accomplished in 23 steps and 4.4% overall yield. The extraordinary configurational lability of the thiazoline segments was overcome by a novel strategy combining the use of the Burgess reagent for multiple simultaneous oxazoline and thiazoline formations and an efficient oxazoline → thiazoline heterocycle interconversion. In addition to the total synthesis, this work highlights the scope of alternative strategies toward Lissoclinum peptides and presents the preparation of analogues for SAR studies of the cytotoxic effects of this family of marine natural products.

Highly active and selective anticoagulants: D-Phe-Pro-Arg-H, a free tripeptide aldehyde prone to spontaneous inactivation, and its stable N-methyl derivative, D-MePhe-Pro-Arg-H

D-Phe-Pro-Arg-H sulfate (GYKI-14166) is a highly active and selective inhibitor of thrombin both in vitro and in vivo. Recent studies on the stability of D-Phe-Pro-Arg-H in neutral aqueous solution at higher temperature have revealed that it is transformed into inactive 5,6,8,9,10,10a-hexahydro-2-(3'-guanidinopropyl)-5-benzyl-6-oxo-imidazo [1,2-a]pyrrolo[2,1-c]pyrazine. No such inactivation could be observed with Boc-D-Phe-Pro-Arg-H (GYKI-14451), but this compound was far less specific than the free peptide as it inhibited thrombin and, for instance, plasmin equally well. Assuming that the transformation of free tripeptide aldehyde, mentioned above, can only be initiated by a primary amino terminus, the N-alkyl derivatives of D-Phe-Pro-Arg-H were prepared. Of the new analogues, D-MePhe-Pro-Arg-H (GYKI-14766) proved to be as highly active and selective anticoagulant as its parent compound and was not inactivated by transformation into a heterocyclic compound.