1337559-31-5

Basic information

• Product Name: 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose
• CAS NO: 1337559-31-5
• Molecular Weight: 1202.84
• Mol File: 1337559-31-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose(1337559-31-5)
• EPA Substance Registry System: 1-deoxy-1-[(2'S,3'S,4'R)-2'-(N-hexacosanoylamino)-3',4'-dihydroxyoctadecyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose(1337559-31-5)

Safety Data

• Hazardous Substances Data: 1337559-31-5(Hazardous Substances Data)

Upstream product

• 1233497-19-2 (R)-heptadec-1-en-3-ol 
• 1233218-77-3 C₂₄H₄₀O₃ 
• 1337559-27-9 1-deoxy-1-[(4'R,2'E)-4'-hydroxy-2'-octadecenyl]-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 
• 1337559-28-0 C₅₂H₇₀O₇ 
• 205371-71-7 cerotic acid para-nitrophenyl ester 
• 1337559-25-7 (R)-1-((heptadec-1-en-3-yloxy)methyl)-4-methoxybenzene 

Relevant articles and documents

Total synthesis of α-1 C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis

A nonisosteric α-C-glycoside analogue of KRN7000 (α-1C-GalCer, 1) was reported to induce a selective type of cytokine release in human invariant natural killer cells in vitro. We report here a very concise synthetic route to 1 and its analogue 1′. The key steps include olefin cross-metathesis, Sharpless asymmetric epoxidation, and epoxide opening by NaN3/NH4Cl. Inversion of configuration at the amide-bearing carbon in the phytosphingosine backbone constructed by epoxide opening in our previous synthesis of 1 was verified, indicating that remote group participation is not involved during the epoxide-opening reaction.