1542131-42-9

Basic information

• Product Name: (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane
• Synonyms: (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane
• CAS NO: 1542131-42-9
• Molecular Weight: 850.27
• Mol File: 1542131-42-9.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane(1542131-42-9)
• EPA Substance Registry System: (2S,3S,4S,5S,6R)-2-azido-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecane(1542131-42-9)

Safety Data

• Hazardous Substances Data: 1542131-42-9(Hazardous Substances Data)

Upstream product

• 1542131-41-8 (2R,3S,4S,5S,6R)-1-tert-butyldimethylsilyloxy-3,4,5,6-(tetrabenzyloxy)octadecan-2-ol 

Downstream Products

• 1542131-43-0 (2S,3S,4S,5S,6R)-2-azido-3,4,5,6-(tetrabenzyloxy)octadecan-1-ol 
• 1542131-45-2 (2S,3S,4S,5S,6R)-2-amino-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside 
• 1542131-44-1 (2S,3S,4S,5S,6R)-2-azido-3,4,5,6-(tetrabenzyloxy)octadecyl 2,3-di-O-benzyl-4,6-O-(di-tert-butyl)silylene-α-d-galactopyranoside 

Relevant articles and documents

Synthesis of RCAI-172 (C6 epimer of RCAI-147) and its biological activity

RCAI-147 is one of the hydroxylated analogues of KRN7000 which is known as a ligand for the activation of CD1d mediated invariant natural killer T cells (iNKT cells) and releases both T helper 1 (Th1) cytokines such as IFN-γ and T helper 2 (Th2) cytokines such as IL-4. KRN7000 has been anticipated as an antitumor drug or an adjuvant for viral infection such as influenza, because of its strong secretion of IFN-γ. In an interesting twist, it has been obvious in our previous paper that RCAI-147 induces much more Th2 cytokines (IL-4) than Th1 cytokines (IFN-γ) from iNKT cells compared to KRN7000, and shows fairly good result in the experimental autoimmune encephalomyelitis (EAE) test. Therefore, synthesis of RCAI-172 (C6-OH epimer of RCAI-147) was attempted to examine the biological activity. As a result, RCAI-172 was synthesized and its biological activity biased to Th2 response largely compared to that of KRN7000. However, this level decreased to approximately 61% compared to that of RCAI-147. And the clinical score of RCAI-172 for EAE suppression was disappointing. There exist seven chiral centers in the aglycon part of RCAI-172, and even though the change of configuration is just one position (C6-OH), the effect on both Th1/Th2 response and EAE test is fairly large.