258326-64-6

Basic information

• Product Name: methyl (R)-4,6-O-benzylidene-2-C-methyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside
• Synonyms: methyl (R)-4,6-O-benzylidene-2-C-methyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside
• CAS NO: 258326-64-6
• Molecular Weight: 320.386
• Mol File: 258326-64-6.mol

Chemical Properties

• CAS DataBase Reference: methyl (R)-4,6-O-benzylidene-2-C-methyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (R)-4,6-O-benzylidene-2-C-methyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside(258326-64-6)
• EPA Substance Registry System: methyl (R)-4,6-O-benzylidene-2-C-methyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside(258326-64-6)

Safety Data

• Hazardous Substances Data: 258326-64-6(Hazardous Substances Data)

Upstream product

• 917-54-4 methyllithium 
• 171076-01-0 methyl 4,6-O-benzylidene-3-deoxy-3-C-methyl-3-C-propenyl-α-D-erythro-hexopyranoside 

Downstream Products

• 258326-65-7 methyl (R)-4,6-O-benzylidene-2-C-methyl-2-O-propenyl-3-deoxy-3-C-propenyl-α-D-glucopyranoside 

Relevant articles and documents

Stereoselective Preparation of Enantiomerically Pure Annulated Carbohydrates Using Ring-Closing Metathesis

Ring-closing metathesis has been applied to a series of glucose derivatives to produce cyclopentene derivatives 5a and 5b, cyclohexene derivatives 8 and 9, cycloheptene 12, and cyclooctene 14. Spirocyclic dihydrofurans 19, 26a, and 26b, along with dihydropyran 22, were also produced. A range of fused oxepine derivatives 29a-c and one oxo-cyclononene 31 were also prepared. Cyclopentene 5b was subjected to a sequence of hydrogenation, NBS bromination, and treatment with powdered zinc to furnish the ring-expanded product 35. No such ring expansion occurred when the cyclohexaannulated compound 8 was treated with NBS followed by powdered zinc, leading to aldehyde 39. The spiro dihydrofuran derivative 19 was converted to the aldehyde 42 via the same reaction sequence used to fragment cyclopentene derivative 5b.