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

Description

(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 is a complex organic compound with a unique molecular structure. It is characterized by its chiral centers at the 2nd, 3rd, and 4th carbon atoms, which are in the R, S, and S configurations, respectively. The molecule contains multiple benzyloxy groups and a 1,3-dioxolan ring, as well as a 4-methylpiperazin-1-yl group attached to the 1st carbon. (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 is an intermediate in the synthesis of Ertugliflozin, a drug used for the treatment of type 2 diabetes.

Uses

Used in Pharmaceutical Industry:
(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 is used as an intermediate in the synthesis of Ertugliflozin (1210344-57-2), an antidiabetic agent. It plays a crucial role in the development of medications for the treatment of type 2 diabetes, helping to manage blood sugar levels and improve the quality of life for patients with this condition.
Additionally, this compound may have potential applications in other areas of the pharmaceutical industry, such as the development of new drugs or the enhancement of drug delivery systems. However, further research and development would be required to explore these possibilities.

Upstream product

• 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 
• 144-62-7 oxalic acid 
• 67-64-1 acetone 

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.