205371-68-2

Usage

Chemical Properties

White Solid

InChI:InChI=1/C56H117NO4Si2/c1-13-15-17-19-21-23-25-27-28-29-30-31-32-33-34-35-36-37-39-41-43-45-47-49-53(59)57-51(50-58)54(61-63(11,12)56(6,7)8)52(60-62(9,10)55(3,4)5)48-46-44-42-40-38-26-24-22-20-18-16-14-2/h51-52,54,58H,13-50H2,1-12H3,(H,57,59)/t51-,52+,54-/m0/s1

Upstream product

• 123-78-4 (2S,3R,4E)-2-amino-4-octadecene-1,3-diol 
• 554-62-1 D-ribo-phytosphingosine 
• 60669-22-9 n-undecyltriphenylphosphonium bromide 
• 1388155-11-0 (R)-2-((tert-butyldimethylsilyl)oxy)hexadecanal 
• 1388155-10-9 (R)-methyl 2-(tert-butyldimethylsilyloxy)hexadecanoate 
• 1388155-16-5 (2S,3S,4R)-1-benzyloxy-3,4-bis-(tert-butyldimethylsilyloxy)-2-hexacosanoylamino-octadecane 
• 1388155-09-6 (R)-methyl 2-(tert-butyldimethylsilyloxy)hexadec-5-enoate 
• 1388155-15-4 (2S,3S,4R)-1-(benzyloxy)-3,4-bis(tert-butyldimethylsilyloxy)octadecan-2-amine 
• 1388155-14-3 tert-butyl (2S,3S,4R)-1-(benzyloxy)-3,4-dihydroxyoctadecan-2-ylcarbamate 
• 1388155-13-2 C₂₅H₄₅NO₃*ClH 
• 1388155-12-1 N-((2S,3S,4R)-1-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-hydroxyoctadecan-2-yl)-2-methylpropane-2-sulfinamide 
• 1244958-79-9 C₁₂H₂₄O₄Si 
• 1017935-14-6 N-[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-2-((2R,3S)-3-tridecyl-oxiranyl)-ethyl]-4-methyl-benzenesulfonamide 
• 205371-66-0 Hexacosanoic acid [(1S,2S,3R)-2-(tert-butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-heptadecyl]-amide 

Downstream Products

• 205371-69-3 (2S,3S,4R)-3,4-bis-tert-butyldimethylsilyloxy-2-hexacosanoylamino-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane 
• 424823-22-3 Hexacosanoic acid [(1S,2S,3R)-1-((2S,3R,4S,5S,6R)-6-azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-2,3-bis-(tert-butyl-dimethyl-silanyloxy)-heptadecyl]-amide 
• 424823-29-0 Hexacosanoic acid [(1S,2S,3R)-1-((2S,3R,4S,5S,6R)-6-aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxymethyl)-2,3-dihydroxy-heptadecyl]-amide 
• 424823-30-3 (2S,3S,4R)-2-hexacosanoylamido-(2,3,4-tri-O-benzyl-6-deoxy-6-azido-α-D-galactopyranosyloxy)octadecane-3,4-diol 
• 1092684-29-1 (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-O-methyl-α-D-galactopyranosyl)octadecane-1,3,4-triol 
• 1092684-36-0 (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-methyl-α-D-galactopyranosyl)octadecane-1,3,4-triol 
• 1092684-34-8 (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-α-D-fucopyranosyl)octadecane-1,3,4-triol 
• 1092684-38-2 (2S,3S,4R)-2-(hexacosanamido)-1-O-(2,3,4-tri-O-benzyl-6-deoxy-6-fluoro-α-D-galactopyranosyl)octadecane-1,3,4-triol 

Relevant academic research and scientific papers

CARBOHYDRATE-GLYCOLIPID CONJUGATE VACCINES

The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

Protein and peptide-free synthetic vaccines against streptococcus pneumoniae type 3

The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

PROTEIN AND PEPTIDE-FREE SYNTHETIC VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE TYPE 3

The present invention provides a protein- and peptide-free conjugate comprising a synthetic carbohydrate and a carrier molecule, wherein the synthetic carbohydrate is a Streptococcus pneumoniae type 3 capsular polysaccharide related carbohydrate and the carrier molecule is a glycosphingolipid. Said conjugate and pharmaceutical composition thereof are useful for immunization against diseases associated with Streptococcus pneumoniae, and more specifically against diseases associated with Streptococcus pneumoniae type 3.

A flexible approach to construct three contiguous chiral centers of sphingolipids, and asymmetric synthesis of d-ribo-phytosphingosine and its derivatives

An efficient approach to build the three contiguous stereogenic centers of sphingosine unit starting from cheap glutamic acid is described. The key step of this approach is the SmI2-mediated cross-coupling of chiral N-tert-butanesulfinyl imine 11 with sterically hindered aliphatic aldehyde 9 or 21 to construct hydroxymethyl β-amino alcohol 10 or 22 in high diastereoselectivity (>99%, de). The utility of this flexible method has been demonstrated in the synthesis of d-ribo-phytosphingosine 1, its two derivatives 18 and 29. Moreover, a practicable synthetic route for synthesis of various sphingolipids, ceramides, α-galactosylceramides and their derivatives is also described.

Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a c

Practical synthesis of KRN7000 from phytosphingosine

The efficient and practical synthesis of die biologically important a-galactosylceramides, KRN7000, from phytosphingosine has been achieved in six steps in high overall yield.

Diastereoselective epoxidation of the double bond at C-4 of sphingosines to provide phytosphingosine relatives such as α-galactosylceramide KRN7000

Diastereoselective epoxidation of the double bond at C-4 of two sphingosine derivatives [3, R = (CH2)7Me or (CH2)12Me] was studied. Dimethyldioxirane was found to be the best oxidant for that purpose. Application of this epoxidation resulted in a new synthesis of the α- galactosylceramide KRN7000 (2), which has an enhancing effect on the activity of natural killer cells.