173346-53-7

Basic information

• Product Name: (E)-2-((2R,3R,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-pent-2-enoic acid methyl ester
• Synonyms: (E)-2-((2R,3R,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-pent-2-enoic acid methyl ester
• CAS NO: 173346-53-7
• Molecular Weight: 618.724
• Mol File: 173346-53-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-2-((2R,3R,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-pent-2-enoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-2-((2R,3R,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-pent-2-enoic acid methyl ester(173346-53-7)
• EPA Substance Registry System: (E)-2-((2R,3R,4S,5R,6R)-3-Acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl)-pent-2-enoic acid methyl ester(173346-53-7)

Safety Data

• Hazardous Substances Data: 173346-53-7(Hazardous Substances Data)

Upstream product

• 153996-35-1 methyl (E)-2-<<(4-nitrobenzoyl)oxy>methyl>-2-pentenoate 
• 133181-02-9 3-hydroxy-2-methylene-pentanoic acid methyl ester 
• 108869-64-3 3,4,6-tri-O-benzyl-2-O-acetyl-α-D-glucosyl trichloroimidate 
• 153996-40-8 methyl (2E)-2-(hydroxymethyl)pent-2-enoate 

Downstream Products

• 173346-51-5 tert-butyl (2R,3R)-2-(N-(benzyloxycarbonyl)amino)-2,3-methanopentanoate 
• 173346-44-6 (2'R,3'R)-2'-<<(triisopropylsilyl)oxy>methyl>-2',3'-methanopentyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 173346-42-4 1-O-<2'-<<(triisopropylsilyl)oxy>methyl>-2'-penten-1'-yl>-3,4,6-tri-O-benzyl-β-D-glucopyranose 

Relevant articles and documents

Stereoselective synthesis of a11 four isomers of coronamic acid: A general approach to 3-methanoamino acids

A general approach to the synthesis of enantiomerically enriched 3-methanoamino acids is presented where the cyclopropyl unit was introduced by a stereoselective cyclopropanation using a D-glucose-derived chiral auxiliary. This methodology was applied to the synthesis of the four stereoisomers of coronamic acid 14, 17, 20, and 22. Starting with the readily available allylic alcohol 5, β-D-glucopyranoses (E)-6 and (Z)-7 have been selectively prepared using trichloroacetimidate 2. These olefins were cyclopropanated with very high diastereoselectivities using Et2Zn/ CH2I2 (≥98% de) and Et2Zn/CH2ICl (≥97% de) in yields greater than 90%. After cleavage of the chiral auxiliary by ring contraction of the 2-O-triflyl derivative of cyclopropanes 8 and 9, cyclopropylmethanols (-)-10 and (+)-11 have been transformed to all four isomeric protected amino acids by selective protecting group manipulations, oxidation of primary alcohols, and Curtius rearrangement.