494869-23-7

Basic information

• Product Name: methyl 4-(3-deoxy-L-glycero-tetronamido)-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside
• Synonyms: methyl 4-(3-deoxy-L-glycero-tetronamido)-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside
• CAS NO: 494869-23-7
• Molecular Weight: 295.308
• Mol File: 494869-23-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 4-(3-deoxy-L-glycero-tetronamido)-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(3-deoxy-L-glycero-tetronamido)-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside(494869-23-7)
• EPA Substance Registry System: methyl 4-(3-deoxy-L-glycero-tetronamido)-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside(494869-23-7)

Safety Data

• Hazardous Substances Data: 494869-23-7(Hazardous Substances Data)

Upstream product

• 19444-84-9 3-deoxy-L-glycero-tetronolactone 
• 381168-36-1 methyl 4-amino-3-fluoro-2-O-methyl-3,4,6-trideoxy-α-D-mannopyranoside 

Relevant articles and documents

Synthetic explorations towards 3-deoxy-3-fluoro derivatives of D-perosamine

Based on a literature precedent, preparation of methyl 4-azido-3,4,6-trideoxy-3-fluoro-α-D-mannopyranoside (18) was attempted via fluorination of methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-altropyranoside with diethylaminosulfur trifluoride (DAST). Contrary to expectations, the reaction took place with retention of configuration at the site of the fluorination yielding methyl 4-azido-2-O-benzyl-3,4,6-trideoxy-3-fluoro-α-D-altropyranoside. Treatment with DAST of methyl 4-azido-2-O-benzyl-4,6-dideoxy-α-D-allopyranoside (8), or its 2-(p-methoxybenzyl) analog 9 resulted in fluorination with inversion of configuration at position 3, to give the corresponding 3-deoxy-3-fluoro glucopyranosides 10 and 11, respectively. Accordingly, compound 18 was prepared from 11, by de-p-methoxybenzylation at O-2, followed by inversion of configuration at C-2 in the resulting methyl 4-azido-3,4,6-trideoxy-3-fluoro-α-D-glucopyranoside. The 2-O-methyl analog of 18 (19) was prepared by methylation of 18. Compounds 18 and 19 were converted, conventionally, into the 3-fluoro analogs of the terminal determinants of the O-PS of Vibrio cholerae O:1, serotype Inaba and Ogawa, respectively.