1431329-06-4

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;(2R,3S,4S)-2,3,4-tris(benzyloxy)-4-(4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-1-(4-methylpiperazin-1-yl)butan-1-oneoxalicacid;(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;EOS-60359;(5xi)-5,6-O-(1-Methylethylidene)-1-C-(4-methyl-1-piperazinyl)-5-C-[(phenylmethoxy)methyl]-2,3,4-tris-O-(phenylmethyl)-D-xylo-hexose ethanedioate (1:1)
• CAS NO: 1431329-06-4
• Molecular Formula: C₂H₂O₄*C₄₃H₅₂N₂O₇
• Molecular Weight: 708.88218
• Mol File: 1431329-06-4.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• 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(1431329-06-4)
• 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(1431329-06-4)

Safety Data

• Hazardous Substances Data: 1431329-06-4(Hazardous Substances Data)

Usage

Uses

(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 is an antidiabetic agent and an Ertugliflozin (1210344-57-2) intermediate.

Upstream product

• 144-62-7 oxalic acid 
• 67-64-1 acetone 
• 1431329-05-3 (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 

Downstream Products

• 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 
• 1431329-05-3 (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 

Relevant articles and documents

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.