1201913-68-9

Usage

Uses

Used in Pharmaceutical Industry:
(1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] is used as a precursor in the synthesis of pharmaceutical compounds due to its complex spirocyclic framework and multiple functional groups, which can be further modified for specific medicinal applications.
Used in Chemical Research:
In the field of chemical research, (1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] serves as a model for studying the effects of stereochemistry on molecular properties and reactivity. Its unique structure allows researchers to explore novel reaction pathways and mechanisms, potentially leading to the discovery of new chemical processes or materials.
Used in Material Science:
The highly functionalized nature of (1S,3′R,4′R,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-3′,4′,5′-tris(methoxycarbonyloxy)-6′-[(methoxycarbonyloxy)methyl]spiro[2-benzofuran-1(3H),2-[2H]pyran] makes it a candidate for the development of new materials with specialized properties. Its potential use in material science could include applications in the creation of advanced polymers, sensors, or other high-tech materials.

Upstream product

• 903565-83-3 (1S,3′R,4′S,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′,4′,5′-triol 
• 79-22-1 methyl chloroformate 
• 90-80-2 D-Glucono-1,5-lactone 
• 32469-28-6 (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one 
• 89980-92-7 (2-bromo-1,4-phenylene) dimethyl carbinol 
• 1019209-73-4 2-bromo-1,4-bis(((2-methoxypropan-2-yl)oxy)methyl)benzene 
• 903566-65-4 (1S,3′R,4′S,5′S,6′R)-3′,4′,5′,6′-tetrahydro-6,6′-bis(hydroxymethyl)spiro[2-benzofuran-1(3H),2-[2H]pyran]-3′,4′,5′-triol 
• 18643-86-2 dimethyl 2-bromoterephthalate 
• 586-35-6 2-bromo-1,4-benzenedicarboxylic acid 
• 63139-21-9 4-ethylphenylboronic acid 

Downstream Products

• 903565-83-3 (1S,3′R,4′S,5′S,6′R)-6-[(4-ethylphenyl)methyl]-3′,4′,5′,6′-tetrahydro-6′-(hydroxymethyl)-spiro[isobenzofuran-1(3H),2′-[2H]pyran]-3′,4′,5′-triol 
• 1201913-74-7 (1S,3'R,4'S,5'R,6'R)-6-(4-ethylbenzyl)-6′-((pivaloyloxy)-methyl)-3',4',5',6'-tetrahydro-3H-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triyl tris(2,2-dimethylpropanoate) 

Relevant academic research and scientific papers

A Scalable Synthesis of Tofogliflozin Hydrate

A newly process for the synthesis of tofogliflozin hydrate, a sodium-glucose cotransporter type 2 (SGLT2) inhibitor, was described. Three improvements were achieved, including the development of a regioselective Friedel-Crafts reaction, a high-yield reduction, and a mild metal-halogen exchange. These improvements ultimately resulted in the isolation of tofogliflozin hydrate as a white solid in >99% purity (HPLC area) and 23% overall yield after 12 steps without column chromatography.

The regioselective bromine-lithium exchange reaction of alkoxymethyldibromobenzene: A new strategy for the synthesis of tofogliflozin as a SGLT2 inhibitor for the treatment of diabetes

The regioselective bromine-lithium exchange reaction of 2,4-dibromo-1-(1-methoxy-1-methylethoxymethyl)benzene (2), which resulted in optimized selectivity of 220:1, is described. Applying this method to the synthesis of tofogliflozin (1) as a SGLT2 inhibi

Method for preparing derivatives of spiroketal

Provided is a process for the preparation of a spiroketal derivative via a compound represented by general formula (II) [wherein each variable group and each variable number are as defined in the description].

Development of a Scalable Synthesis of Tofogliflozin

An efficient and scalable synthesis of an antidiabetic drug, tofogliflozin (1), which was identified as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor, is described. A key factor in the synthesis of 1 was the selection of the purpose-designed protecting group, which plays a strategic role in protection, chemoselective activation, and crystalline purification. The developed and optimized method made it possible to prepare 1 on a multidecagram scale without any column chromatography.

CRYSTAL OF SPIROKETAL DERIVATIVE, AND PROCESS FOR PRODUCTION THEREOF

The present invention provides a process for preparing a spiroketal derivative, via an intermediate represented by Formula (VI): wherein variable groups and numbers are as defined in the specification, which can be produced from dihalobenzene derivatives in one pot reaction.