1431329-05-3

Basic information

• Product Name: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one
• Synonyms: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one
• CAS NO: 1431329-05-3
• Molecular Weight: 708.895
• Mol File: 1431329-05-3.mol

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one(1431329-05-3)
• EPA Substance Registry System: (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one(1431329-05-3)

Safety Data

• Hazardous Substances Data: 1431329-05-3(Hazardous Substances Data)

Upstream product

• 1520112-88-2 (2R,3S,4S)-2,3,4,6-tetrakis(benzyloxy)-1-(4-methylpiperazin-1-yl)hexane-1,5-dione 
• 1431329-06-4 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one oxalate 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 1431329-06-4 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one oxalate 
• 1629222-50-9 (2S,3S,4R)-2,3,4-tris(benzyloxy)-1-((benzyloxy)-methyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane 
• 1210344-57-2 Ertugliflozin 
• 1298086-20-0 ((1R,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)-phenyl)-2,3,4-trihydroxy-6,8-dioxabicyclo[3.2.1]octan-1-yl)methyl acetate 
• 1210344-83-4 (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid 
• 1431329-07-5 (2R,3S,4S)-2,3,4-tris(benzyloxy)-4-((R)-4-((benzyloxy)-methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-one 

Relevant articles and documents

METHODS FOR PREPARING SGLT2 INHIBITORS

This invention relates to methods for preparing a sodium-glucose transporter 2 (SGLT2) inhibitor, a cocrytalline SGLT2 and (S)-5-oxopyrrolidine-2-carboxylic acid (L-PGA) complex, and intermediates useful in the preparation of the said SGLT2 inhibitor.

Commercial route research and development for SGLT2 inhibitor candidate ertugliflozin

A practical synthesis of SGLT2 inhibitor candidate ertugliflozin (1) has been developed for potential commercial application. The highly telescoped process involves only three intermediate isolations over a 12-step sequence. The dioxabicyclo[ 3.2.1]octane motif is prepared from commercially available 2,3,4,6-tetra-O-benzyl-D-glucose, with nucleophilic hydroxymethylation of a 5-ketogluconamide intermediate as a key step. The aglycone moiety is introduced via aryl anion addition to a methylpiperazine amide. High chemical purity of the API is assured through isolation of the crystalline penultimate intermediate, tetraacetate 39. A cocrystalline complex of the amorphous solid 1 with L-pyroglutamic acid has been prepared in order to improve the physical properties for manufacture and to ensure robust API quality.