62641-00-3

Basic information

• Product Name: <4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
• Synonyms: <4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone
• CAS NO: 62641-00-3
• Molecular Weight: 430.5
• Mol File: 62641-00-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: <4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: <4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone(62641-00-3)
• EPA Substance Registry System: <4S,5R>-2,4,6-tribenzyloxy-5-hydroxyhex-2-enoic acid-1,5-lactone(62641-00-3)

Safety Data

• Hazardous Substances Data: 62641-00-3(Hazardous Substances Data)

Upstream product

• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 79834-15-4 (2-bromo-3,5-bis(methoxymethoxy)phenyl)methanol 
• 67-66-3 chloroform 
• 82598-88-7 2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone 
• 64-17-5 ethanol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 362623-58-3 methyl 3-azido-3-deoxy-2,4,6-tri-O-benzyl-α-D-altro-hexopyranoside 
• 100-39-0 benzyl bromide 
• 20379-58-2 methyl 3-azido-3-deoxy-α-D-altropyranoside 

Downstream Products

• 16134-31-9 2.4.6-Tri-O-benzyl-3-desoxy-L-threo-hex-2-enopyranose 
• 16134-30-8 2,4,6-Tri-O-benzyl-3-desoxy-N,N-dimethyl-L-threo-hexen-2-onamid 

Relevant articles and documents

C-2 Epimerization of aldonolactones promoted by magnesium iodide: a new way towards non-enzymatic epimerization

The first example of a non-enzymatic C-2 epimerization of aldonolactones is reported. The reaction of 2,3,4,6-tetra-O-benzyl-d-gluconolactone or 2,3,4,6-tetra-O-benzyl-d-mannonolactone with MgI2 in EtOH afforded their respective C-2 epimer. Studies conducted in EtOD showing the incorporation of a deuterium atom only at the C-2 position of the epimerized product reveal an epimerization rather than a racemization reaction. A mechanism involving a chelation with a magnesium species is proposed to explain this C-2 inversion reaction.

Preparation and reactivity of some 3-deoxy-D-altronic acid derivatives

3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was the key intermediate in the preparation of poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl)propanamide], a chiral nylon 3 analog. We now describe an alternative synthetic route

Synthesis of the papulacandin C-arylglucosyl spiroketal nucleus

The enantiomerically pure tricyclic C-arylglucosyl spiroketal nucleus of papulacandin has been synthesized by reaction of an appropriately protected gluconolactone 4 with a metalated derivative of 5-(hydroxymethyl)resorcinol (5). In model studies, alkylli