Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

Fan, Gang-Ting; Pan, Yi-Shin; Lu, Kuo Chang; Cheng, Yu‐Ting; Lin, Wan‐Chen; Lin, Steven; Lin, Chung-Wei; Wong, Chi‐Huey; Fang, Jim‐Min; Lin, Chun‐Cheng

doi:10.1016/j.tet.2004.12.027

Cited by 74 publications

(41 citation statements)

References 48 publications

(25 reference statements)

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“…After the disclosure of the structure 1 by Kirin Brewery, 4) many reports on the synthesis of 1 were published from 1995 to 2011, [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44] including practical synthesis of it by Kirin group. 25) As shown in Fig.…”

Section: Synthesis Of Krn7000mentioning

confidence: 99%

“…Hence the synthesis of 1 includes two key steps: -selective (or -specific) galactosylation, and the construction of three continuous asymmetric centers of the phytosphingosine chain. To connect a galactose part in -orientation, researchers have used 1-OH free garactopyranose (D), 30,33,44) thiogalactoside (E), 28,30,36,37,41) galactosyl trichloroacetimidate (F), [27][28][29][32][33][34]36,39,43) phosphite (G), 33) phosphate (H), 42) acetate (I), 37) or halide (J) as the galactose donor. 4,25,26,29,31,35,38,40) Hague, 31) and trichloroacetimidate (L) with trimethylsilyl triflate (60%) reported by Kimura et al, 32) gave the highest -stereoselectivity (exclusivity).…”

Section: Synthesis Of Krn7000mentioning

confidence: 99%

“…It is also difficult to shorten or elongate its chain length. To synthesize a versatile intermediate that can be converted to many types of analogs of 1 for investigation of structure-activity relationships, many research groups have employed L-serine (M), 39) D-tartaric acid (N), 37) or sugars, such as 25,[30][31][32]40) as suitable chiral sources for building the (2S,3S,4R)-2-amino-1,3,4-triol unit. Takikawa et al prepared B from D-erythro-sphingosine (U), which was synthesized from Garner's aldehyde (V), by stereoselective epoxidation, followed by regioselective epoxide-ring opening.…”

Section: Synthesis Of Krn7000mentioning

confidence: 99%

“…89) According to Fan et al, galactosyl serine analog 23 showed weak bioactivity, and therefore a hydroxy group at the 3-position is preferable as a proton donor to a carbonyl group in making a stable CD1d/ligand complex. 30 45) and is commercially available at a reasonable price. Hence, KRN7000 (1) is thought to have a rational structure.…”

Section: 4886)mentioning

confidence: 99%

“…91) Isosteric replacement of the 2-amide moiety of 1 with a 1,2,3-triazole group (28) and with an ester (29) has been reported, 92,93) and this led to Th2-type cytokine production by the analogs. In addition, a sulfonamido analog (30) and an ,-difluoroacylated one (31) with an acidic amide NH also showed the Th2-biased cytokine response. 94,95) We also found that an ureido analog (32) induced Th1-type cytokine production.…”

Section: 4886)mentioning

confidence: 99%

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Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

Tashiro

2012

Bioscience, Biotechnology, and Biochemistry

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Section: Synthesis Of Krn7000mentioning

confidence: 99%

Section: Synthesis Of Krn7000mentioning

confidence: 99%

Section: Synthesis Of Krn7000mentioning

confidence: 99%

Section: 4886)mentioning

confidence: 99%

Section: 4886)mentioning

confidence: 99%

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Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

Tashiro

2012

Bioscience, Biotechnology, and Biochemistry

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Staudinger Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The reaction between an azide and triphenylphosphine (or phosphonite) to produce an iminophosphorane (the nucleophilic aza ‐ylide) and subsequent hydrolysis to yield a primary amine is generally known as the Staudinger reaction. This reaction is a specific, high‐yielding reaction in which the iminophosphorane intermediate hydrolyzes spontaneously in the presence of water. The most important modification of Staudinger reaction is probably its extension to the formation of peptide bonds, employing the high nucleophilicity of nitrogen atom in aza y‐lide in the presence of an ester group. This reaction has been applied in organic synthesis, especially in the preparation of peptide bonds in a living system.

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Wittig Reaction

2010

Comprehensive Organic Name Reactions and Reagents

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The synthesis of an olefin from the reaction between a carbonyl compound (aldehyde or ketone) and a phosphonium ylide, via either a betaine and/or oxaphosphetane intermediate is generally known as the Wittig reaction. Occasionally, it is also referred to as the Wittig alkenylation or Wittig process. The extension of this reaction by the application of a phosphine oxide carbanion, instead of a phosphonium ylide is known as the Horner reaction or Wittig Horner reaction, while the preparation of olefin from a phosphonate carbanion is commonly referred to as the Horner–Wadsworth–Emmons olefination. Several other extensions of this reaction have been addressed. All the reaction steps of the Wittig reaction have been discussed. The reversible process to give the carbonyl compound and phosphorane is also possible, and such reversible reaction is known as the retro ‐Wittig reaction. The most important feature of the Wittig reaction is probably the easy control of stereochemistry of olefins (i.e., either Z ‐ or E ‐configuration). It has been observed that ultimate configuration of olefins depends on many factors, such as the structure of phosphoranes, the base and the solvent used, the concentration of ylide, and the reaction temperature. In particular, the Z ‐selectivity from nonstabilized ylides can be further enhanced by replacement of the phenyl group in triphenylphosphane moiety with either a 2‐pyridyl or 2‐furyl group. It has been reported that even the replacement of one phenyl ring by a pyridyl group can apparently increase the Z ‐selectivity without affecting the yields of olefins. It has been reported that E ‐olefin is the major product in the protic solvent, whereas Z ‐olefin predominates in the Wittig reactions when carried out in aprotic media. Other facets of the Wittig reaction have also been discussed, which include, application of the catalysts and the enhancement of reactivity in organic solvent by the application of a phase‐transfer catalyst or promotion of the reaction by photochemical or microwave irradiation. This reaction has very wide applications in organic synthesis, such as transformation of unprotected carbohydrates and preparation of artificial carbon‐linked (1,6)‐oligosaccharides.

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Synthesis of α-galactosyl ceramide and the related glycolipids for evaluation of their activities on mouse splenocytes

Cited by 74 publications

References 48 publications

Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

Structure-Activity Relationship Studies of Novel Glycosphingolipids That Stimulate Natural Killer T-Cells

Staudinger Reaction

Wittig Reaction

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