153496-00-5

Basic information

• Product Name: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol
• Synonyms: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol
• CAS NO: 153496-00-5
• Molecular Weight: 446.543
• Mol File: 153496-00-5.mol

Chemical Properties

• CAS DataBase Reference: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol(153496-00-5)
• EPA Substance Registry System: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-D-lyxo-hex-1-enitol(153496-00-5)

Safety Data

• Hazardous Substances Data: 153496-00-5(Hazardous Substances Data)

Upstream product

• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 21193-75-9 D-galactal 
• 4098-06-0 triacetyl-D-galactal 
• 136982-88-2 (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbaldehyde 

Downstream Products

• 153081-98-2 methyl 3,4,6-tri-Obenzyl-2-deoxy-2-C-methylene-α-D-lyxo-hexopyranoside 
• 1207741-69-2 1,5-anhydro-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-D-lyxo-hexopyranosyl)-2-deoxy-4,6-O-isopropylidene-D-arabino-hex-1-enitol 
• 1092103-69-9 (2S,4R,5R,6R)-2-(allyloxy)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-methylenetetrahydro-2H-pyran 
• 1207741-71-6 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-C-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-α-D-lyxo-hexopyranosyloxy)-methyl-D-lyxo-hex-1-enitol 
• 1207741-68-1 6-O-(3,4,6-tri-O-benzyl-2-deoxy-2-C-methylene-D-lyxo-hexopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 1265884-06-7 C₂₈H₃₀O₅ 
• 1265884-07-8 (3R,4S,5R)-3,4,6-tris(benzyloxy)-5-hydroxy-2-hydroxymethylhex-1-ene 
• 1265884-13-6 (2S,3S,4R)-1-(2'-hydroxyethyl)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-C-methylene-piperidine 

Relevant articles and documents

A New Ferrier System: 2-C-Acetoxymethylglycals. A Convenient Entry to 2-C-Methylene Glycosides

Synthesis of tri-O-benzyl-2-C-acetoxymethylglycals and subsequent Ferrier rearrangement to give 2-C-methylene glycosides is described.

IN VIVO ASSEMBLY OF ASGPR BINDING THERAPEUTICS

Compounds are provided that assemble together in vivo to form an ASGPR-binding compound that has an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein.

Synthesis of dihydroxymethyl dihydroxypyrrolidines and steviamine analogues from C-2 formyl glycals

Synthesis of dihydroxymethyl dihydroxypyrrolidines from C-2 formyl d-glycals has been described via a common dicarbonyl intermediate. The hence obtained pyrrolidines have been further utilized for the synthesis of some steviamine analogues. The newly synthesized molecules have been evaluated for glycosidase inhibition against 6 commercially available enzymes and found to be active in the micromolar range, where one of the steviamine analogues showed good and selective inhibition of β-mannosidase (Helix pomatia).

Mitsunobu Reaction of 1,5-Anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-hex-1-enitols and 1,5-Anhydro-2-deoxy-4,6-O-protected-hex-1-enitols. A Novel Method for the Synthesis of 2-C-Methylene Glycosides and an Useful Alternative to Ferrier Rearrangeme

A simple and convenient method for the synthesis of aryl-3,4,6-tri-O-benzyl-2-deoxy-2-methylene-hexopyranosides 5, 6 and 7, glycosides which are not accessible by the conventional Ferrier rearrangement, has been described based on the Mitsunobu reaction o