A rapid, efficient synthesis of oxytocin and [8-arginine]-vasopressin. Comparison of benzyl, p-methoxybenzyl, and p-methylbenzyl as protecting groups for cysteine

1977 ◽  
Vol 42 (22) ◽  
pp. 3556-3561 ◽  
Author(s):  
David H. Live ◽  
William C. Agosta ◽  
David Cowburn
Keyword(s):  
Arginine Vasopressin ◽  
Protecting Groups ◽  
Efficient Synthesis

Synthesis of oxytocin, arginine-vasopressin and its deamino-analogue using 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur

1981 ◽  
Vol 46 (1) ◽  
pp. 286-299 ◽  
Author(s):  
František Brtník ◽  
Milan Krojidlo ◽  
Tomislav Barth ◽  
Karel Jošt
Keyword(s):  
Peptide Synthesis ◽  
Hydrogen Fluoride ◽  
Sulfur Atom ◽  
Arginine Vasopressin ◽  
Liquid Hydrogen ◽  
Trifluoromethanesulfonic Acid ◽  
Protecting Groups ◽  
Mild Conditions

Preparation of oxytocin, arginine-vasopressin and its deamino-analogue serves as an example of use of 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur atom in the peptide synthesis. This modified benzyl group is sufficiently stable under conditions of solvolytic removal of common amino-protecting groups and it can be cleaved off under mild conditions with liquid hydrogen fluoride or trifluoromethanesulfonic acid.

scholarly journals The Efficient Synthesis of Azasugars from Pentoses

2021 ◽  
Author(s):  
◽  
Michael Meijlink
Keyword(s):  
Clinical Trials ◽  
Biological Properties ◽  
Protecting Groups ◽  
Synthetic Route ◽  
Efficient Synthesis ◽  
Atom Economy ◽  
Total Syntheses ◽  
Structural Analogues ◽  
Original Procedure ◽  
Synthetic Routes

<p>Azasugars [e.g., 1-deoxy-aza-xylopyranose (1) Figure 1] are structural analogues of sugars [e.g., α-D-xylopyranose (2)] where the ring oxygen is substituted by a nitrogen atom. The resemblance of azasugars to their carbohydrate counterparts gives them various biological properties, such as the inhibition of glycosidase and glycosyltransferase enzymes, and as such, these compounds have been in clinical trials for the treatment of AIDS, diabetes,and cancer. Synthetic routes to azasugars have often involved the use of protecting groups, and therefore have generally reduced efficiency by requiring additional steps to apply or remove protecting groups or requiring adjustment of stereochemistry during the synthesis. This thesis presents the first example of a synthesis of four sterochemically different piperidine triols through a four-step methodology minimising the use of protecting groups starting from pentoses. The synthesis of D-xylose derived (3R,4r,5S)-piperidine triol was previously obtained in 40% yield over five steps, but was afforded in 45% overall yield over four steps using the methodology described within this thesis. Next, D-ribose derived (3R,4s,5S)-piperidine triol was obtained in 40% overall yield over four steps, which afforded a vast improvement on the previous most efficient synthetic route obtaining the azasugar in 24% yield over four steps. This four-step three-pot methodology has thus allowed for the synthesis of these piperidine triols in overall yields ranging from 4-69%, surpassing previous total syntheses in efficiency and improving overall atom economy. To further probe the applicability of the methodology, N-alkyl analogues (such as butyl-, phenylethyl-, and hydroxyethyl-analogues) of all four different piperidine triols were synthesised in comparable or greater overall yields compared to literature reports without any required adaptation to the original procedure. Included in these N-alkyl analogues are seven novel azasugars which were obtained in overall yields ranging from 6-35%.</p>

ChemInform Abstract: Efficient Synthesis of Photolabile Alkoxy Benzoin Protecting Groups.

ChemInform ◽  
2010 ◽  
Vol 27 (17) ◽  
pp. no-no
Author(s):  
M. H. B. STOWELL ◽  
R. S. ROCK ◽  
D. C. REES ◽  
S. I. CHAN
Keyword(s):  
Protecting Groups ◽  
Efficient Synthesis

Protecting-Group-Directed Regio- and Stereoselective Oxymercuration–Demercuration: Synthesis of Piperidine Alkaloids Containing 1,2- and 1,3-Amino Alcohol Units

Synthesis ◽  
2017 ◽  
Vol 50 (05) ◽  
pp. 1113-1122 ◽  
Author(s):  
Santosh Tilve ◽  
Sandesh Bugde ◽  
Prajesh S.Volvoikar
Keyword(s):  
Amino Alcohol ◽  
Protecting Groups ◽  
Protecting Group ◽  
Efficient Synthesis ◽  
Piperidine Alkaloids ◽  
Naturally Occurring ◽  
Pipecolinic Acid

An efficient synthesis of naturally occurring 1,2- and 1,3-amino alcohol unit containing 2-substituted piperidine alkaloids and their analogues has been developed from l-pipecolinic acid. The protocol describes the regio- and stereoselective oxymercuration–demercuration of 2-alkenyl piperidines based on protecting groups to give piperidine alkaloids as a key step.

scholarly journals An Efficient Synthesis of 2'-O-(β-D-Ribofuranosyl)biopterin

Pteridines ◽  
2008 ◽  
Vol 19 (1) ◽  
pp. 72-78 ◽  
Author(s):  
Tadashi Hanaya ◽  
Kiyoshi Torigoe ◽  
Kazuyuki Soranaka ◽  
Hiroshi Fujita ◽  
Wolfgang Pfleiderer ◽  
...  
Keyword(s):  
Protecting Groups ◽  
Efficient Synthesis

AbstractN2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1',2'-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2'-O-(2,3,5-tri-Oacetyl- and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2'-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.

Efficient synthesis of carbapenems via the oxalimide cyclization. Manipulation of protecting groups at the oxalimide stage

1995 ◽  
Vol 36 (26) ◽  
pp. 4563-4566 ◽  
Author(s):  
Steven A King ◽  
Brenda Pipik ◽  
Andrew S Thompson ◽  
Ann DeCamp ◽  
Thomas R Verhoeven
Keyword(s):  
Protecting Groups ◽  
Efficient Synthesis

scholarly journals Direct Access to Mono-Protected Homoallylic 1,2-Diols via Dual Chromium/ Photoredox Catalysis

2020 ◽  
Author(s):  
Felix Schäfers ◽  
Linda Quach ◽  
J. Luca Schwarz ◽  
Mar Saladrigas ◽  
Constantin G. Daniliuc ◽  
...  
Keyword(s):  
Functional Group ◽  
Protecting Groups ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Efficient Synthesis ◽  
Enol Ethers ◽  
Silyl Enol Ethers

<p>A dual catalytic strategy enables the efficient synthesis of mono-protected homoallylic 1,2-diols by coupling abundant aldehydes with simple (silyl) enol ethers, thus providing direct access to this important motif without the (super)stoichiometric use of prefunctionalized metal-allyl species. A variety of silyl- and alkyl-based protecting groups is shown and functional group tolerance, chemoselectivity and scalability are highlighted. </p>

Synthesis and use of benzyl tert-butyl iminodicarbonate, a versatile reagent for the preparation of amines

1988 ◽  
Vol 53 (11) ◽  
pp. 2778-2786 ◽  
Author(s):  
Leif Grehn ◽  
Ulf Ragnarsson
Keyword(s):  
Benzyl Alcohol ◽  
Sodium Salt ◽  
Title Compound ◽  
Protecting Groups ◽  
Efficient Synthesis ◽  
Tert Butyl ◽  
Mild Conditions ◽  
High Yields ◽  
Versatile Reagent

An efficient synthesis of benzyl tert-butyl iminodicarbonate (IV), starting from benzoyl isocyanate, is reported. Reaction of the isocyanate with benzyl alcohol gave benzyl N-benzoylcarbamate (II) which on exhaustive tert-butoxycarbonylation via the non-isolated triacyl amine III, after aminolysis, provided the title compound. The sodium salt V was alkylated with various halides under Gabriel conditions to give in high yields the corresponding benzyloxycarbonyl tert-butoxycarbonyl diprotected amines. Similarly, compound IV was alkylated with alcohols under Mitsunobu conditions to give some additional amines of this type, from which the protecting groups can be removed selectively under mild conditions.

Efficient Synthesis of the Anticancer Drug Etoposide 4‘-Phosphate:  Use of Benzylic Ether-Protecting Groups on the Carbohydrate Segment1

2000 ◽  
Vol 4 (1) ◽  
pp. 34-42 ◽  
Author(s):  
Lee J. Silverberg ◽  
John L. Dillon ◽  
Purushotham Vemishetti ◽  
Paul D. Sleezer ◽  
Robert P. Discordia ◽  
...  
Keyword(s):  
Anticancer Drug ◽  
Protecting Groups ◽  
Efficient Synthesis ◽  
Benzylic Ether
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