639476-04-3

Basic information

• Product Name: (4R,5S,6R,7R,8R)-N⁴-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene
• Synonyms: (4R,5S,6R,7R,8R)-N⁴-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene
• CAS NO: 639476-04-3
• Molecular Weight: 481.632
• Mol File: 639476-04-3.mol

Chemical Properties

• CAS DataBase Reference: (4R,5S,6R,7R,8R)-N⁴-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S,6R,7R,8R)-N⁴-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene(639476-04-3)
• EPA Substance Registry System: (4R,5S,6R,7R,8R)-N⁴-benzyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene(639476-04-3)

Safety Data

• Hazardous Substances Data: 639476-04-3(Hazardous Substances Data)

Upstream product

• 1730-25-2 allylmagnesium bromide 
• 114743-85-0 methyl 3,4:5,6-di-O-isopropylidene-D-gluconate 
• 212832-94-5 Methyl 3,4:5,6-di-O-isopropylidene-2-O-(benzyl)-D-gluconate 
• 90-80-2 D-Glucono-1,5-lactone 
• 276238-73-4 2-O-benzyl-3,4:5,6-di-O-isopropylidene-D-glucitol 
• 639476-02-1 (R)-Benzyloxy-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetaldehyde 

Downstream Products

• 639476-07-6 (2RS,4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidenenonan-2-ol 
• 639476-08-7 (4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-1,5-bis(benzyloxy)-6,7:8,9-di-O-isopropylidene-2-oxononane 
• 639476-10-1 N-benzyl-N-((2S,3R,5S,7R)-2-(benzyloxy)-5-((benzyloxy)methyl)-7-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6,8-dioxabicyclo[3.2.1]octan-3-yl)acetamide 
• 639476-09-8 N-Benzyl-N-[(1R,2S,3R,5R,7R)-2-benzyloxy-5-benzyloxymethyl-7-((R)-1,2-dihydroxy-ethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-yl]-acetamide 
• 639476-06-5 (2RS,4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidenenonane-1,2-diol 
• 130525-58-5 methyl 5-acetamido-4-azido-6-(1,2,3-triacetoxypropyl)-5,6-dihydro-4H-pyran-2-carboxylate 
• 639476-05-4 (4R,5S,6R,7R,8R)-N⁴-benzyl-N⁴-acetyl-5-benzyloxy-6,7:8,9-di-O-isopropylidene-1-nonene 

Relevant articles and documents

Synthesis of 4-azido-4-deoxy-neu5,7,8,9ac42en1me. A key intermediate for the synthesis of GG167 from D-glucono-δ-lactone

Stereoselective synthesis of 5-acetamido-7,8,9-tri-O-acetyl-2,6-anhydro-4- azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic acid methyl ester, an advanced key intermediate for the synthesis of neuraminidase inhibitor GG167 (Zanamivir, Relenza), was accomplished using D-glucono-δ-lactone as starting material. A highly diastereoselective allyllation of an imine intermediate, a regioselective azide-opening of an aziridine, and chemoselective oxidations of vicinal diols served successfully as key steps.

Synthesis of a New Stable Conformationally Constrained 2,7-Anhydrosialic Acid Derivative

A stereoseletive synthesis of 2,7-anhydrosialic acid derivative 18 was achieved from D-glucono-δ-lactone. A highly syn-selective addition of Grignard reagent to the N-benzylimine 8 served as a key step.