171076-04-3

Basic information

• Product Name: methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxopropyl)-glucopyranosid-2-ulose
• Synonyms: methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxopropyl)-glucopyranosid-2-ulose
• CAS NO: 171076-04-3
• Molecular Weight: 320.342
• Mol File: 171076-04-3.mol

Chemical Properties

• CAS DataBase Reference: methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxopropyl)-glucopyranosid-2-ulose(CAS DataBase Reference)
• NIST Chemistry Reference: methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxopropyl)-glucopyranosid-2-ulose(171076-04-3)
• EPA Substance Registry System: methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxopropyl)-glucopyranosid-2-ulose(171076-04-3)

Safety Data

• Hazardous Substances Data: 171076-04-3(Hazardous Substances Data)

Upstream product

• 131529-45-8 methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-enyl)-α-D-altropyranoside 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 
• 135700-48-0 methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose 

Downstream Products

• 838838-33-8 methyl α-D-2-amino-4,6-O-((R)-benzylidene)-2,3-dideoxy-2-N,3-C-((2S)-propane-2,3-diyl)-2-N-isopropyl-mannopyranoside 

Relevant articles and documents

Stereoselective synthesis by double reductive amination ring closure of novel aza-heteroannulated sugars

We present here the stereoselective synthesis of a series of 2/3-N-pyrrolidine derivatives of glycosides produced by diastereoselective double reductive amination ring closure of 1,4-dicarbonyl compounds. These precursors were produced by tandem ozonolysi

Ring-closing double reductive amination route to aza-heteroannulated sugars

1,4-Dicarbonyl derivatives of glycosides are produced by ozonolysis or Wacker oxidation. A stable ozonide is isolated and a carbonyl group reduced whilst maintaining the ozonide functionality. The 1,4-dicarbonyl compounds are converted to various N-substi

The stereoselective preparation of an enantiomerically pure cyclopentane using intramolecular aldol cyclopentaannulation of a glucose derivative

Methods for the annulation of carbohydrates have found extensive applications in organic synthesis. We report here a new protocol for the stereoselective conversion of glucose into an enantiomerically pure cyclopentane aldehyde 22. The readily available epoxide 15 was reacted with allyl Grignard to produce alcohol 16 in 86% yield. Swern oxidation followed by epimerization using triethylamine in N,N-dimethylformamide furnished the ketone 17 also in 86% yield. Regioselective deprotonation with lithium hexamethyldisilazane in THF was followed by methylation with methyl iodide and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone as cosolvent to give 80% yield of ketone 18. Oxidation of ketone 18 by the Wacker procedure gave the 1,4-diketone 19 in 56% yield. Intramolecular aldol condensation occurred readily on treatment of diketone 19 with potassium tert-butoxide in toluene to furnish a 90% yield of enone 20. Treatment with N-bromosuccinimide produced the bromoester 21 in 72% yield, which was reduced to a mixture of aldehydes 22 (61%) and 23 (14%) with zinc shot in 2-propanol.

The Synthesis and X-Ray Crystal Structure of a Cyclopentaannulated Sugar; the First Example of an Intramolecular Aldol Cyclopentaannulation in Carbohydrate Chemistry

A 1,4-dicarbonyl compound 5 has been constructed by a sequence involving opening of a protected glucose epoxide with allyl magnesium chloride, alkylation and Wacker oxidation; the 1,4-dicarbonyl compound readily undergoes cyclisation under basic condition