1417141-85-5

Basic information

• Product Name: tert-butyl (2S,3R,E)-3-(benzyloxy)-9-hydroxy-1-(phenylthio)non-5-en-2-ylcarbamate
• CAS NO: 1417141-85-5
• Molecular Weight: 471.661
• Mol File: 1417141-85-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: tert-butyl (2S,3R,E)-3-(benzyloxy)-9-hydroxy-1-(phenylthio)non-5-en-2-ylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (2S,3R,E)-3-(benzyloxy)-9-hydroxy-1-(phenylthio)non-5-en-2-ylcarbamate(1417141-85-5)
• EPA Substance Registry System: tert-butyl (2S,3R,E)-3-(benzyloxy)-9-hydroxy-1-(phenylthio)non-5-en-2-ylcarbamate(1417141-85-5)

Safety Data

• Hazardous Substances Data: 1417141-85-5(Hazardous Substances Data)

Upstream product

• 1576-85-8 4-pentenyl acetate 
• 1417141-82-2 tert-butyl (2S,3R)-3-(benzyloxy)-1-(phenylthio)hex-5-en-2-ylcarbamate 
• 1206532-36-6 tert-butyl (2R,3R)-3-(benzyloxy)-1-hydroxyhex-5-en-2-ylcarbamate 
• 882-33-7 diphenyldisulfane 
• 1417141-61-7 tert-butyl (4R,5R)-4-allyl-2-phenyl-1,3-dioxan-5-ylcarbamate 

Relevant articles and documents

D-glucosamine-derived synthons for assembly of l - Threo -sphingoid bases. Total synthesis of rhizochalinin C

A five-step transformation of d-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of l-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, two-headed sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.