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1298086-18-6

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  • high quality (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyltriacetate

    Cas No: 1298086-18-6

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  • (1R,2S,3S,4R,5S)-1-(ACETOXYMETHYL)-5-(4-CHLORO-3-(4-ETHOXYBENZYL)PHENYL)-6,8-DIOXABICYCLO[3.2.1]OCTANE-2,3,4-TRIYLTRIACETATE

    Cas No: 1298086-18-6

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  • (1R,2S,3S,4R,5S)-1-(Acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl Triacetate

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  • (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

    Cas No: 1298086-18-6

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1298086-18-6 Usage

Description

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyltriacetate is a complex organic compound with a specific stereochemistry. It is characterized by its unique molecular structure, which includes acetoxymethyl, chloro, and benzyl groups attached to a bicyclic core. (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyltriacetate is known for its potential applications in the pharmaceutical industry, particularly as an intermediate in the synthesis of Ertugliflozin, a drug used for treating type 2 diabetes.

Uses

1. Used in Pharmaceutical Industry:
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyltriacetate 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 this medication, which helps manage blood sugar levels in patients with type 2 diabetes.
2. Used in Anticancer Applications (if applicable):
Although the provided materials do not mention any anticancer applications for this specific compound, it is worth noting that compounds with similar structures may have potential uses in cancer research and drug development. Further studies and investigations would be required to explore these possibilities.
3. Used in Drug Delivery Systems (if applicable):
Similarly, the provided materials do not mention any drug delivery applications for this compound. However, given its complex structure and potential pharmaceutical uses, it is plausible that this compound or its derivatives could be investigated for their utility in drug delivery systems in the future.

Check Digit Verification of cas no

The CAS Registry Mumber 1298086-18-6 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,9,8,0,8 and 6 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 1298086-18:
(9*1)+(8*2)+(7*9)+(6*8)+(5*0)+(4*8)+(3*6)+(2*1)+(1*8)=196
196 % 10 = 6
So 1298086-18-6 is a valid CAS Registry Number.

1298086-18-6Synthetic route

Ertugliflozin
1210344-57-2

Ertugliflozin

acetic anhydride
108-24-7

acetic anhydride

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
1298086-18-6

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Conditions
ConditionsYield
With pyridine In toluene at 5 - 20℃; for 24.25h; Inert atmosphere;89%
With pyridine In toluene at 5 - 20℃; for 24.25h;5.4%
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
1298086-18-6

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Ertugliflozin
1210344-57-2

Ertugliflozin

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 0.25h;
With sodium methylate In methanol at 20℃; for 3.25h; Inert atmosphere;
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
1298086-18-6

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

((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
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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium methylate / methanol / 0.25 h / 20 °C
2: pyridine / toluene / 8.28 h / -10 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / methanol / 3.25 h / 20 °C / Inert atmosphere
2: pyridine / toluene / 19.1 h / -10 - 20 °C / Inert atmosphere
View Scheme
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
1298086-18-6

(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

(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
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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium methylate / methanol / 0.25 h / 20 °C
2.1: methanol; water; isopropyl alcohol / 40 - 60 °C / 30 Torr
2.2: 40 - 80 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium methylate / methanol / 3.25 h / 20 °C / Inert atmosphere
2: water; isopropyl alcohol / 10 h / 40 - 80 °C / Inert atmosphere
View Scheme

1298086-18-6Relevant articles and documents

AN EFFICIENT PROCESS FOR THE PREPARATION OF ERTUGLIFLOZIN L-PYROGLUTAMIC ACID AND INTERMEDIATES THEREOF

-

Page/Page column 5; 16; 19, (2021/07/10)

The present invention relates to an efficient process for the preparation of Ertugliflozin L-pyroglutamic acid of formula (I) and intermediate thereof, in environment friendly conditions. The present invention further relates to a process for the preparation of substantially pure intermediate of formula (IV).

Commercial route research and development for SGLT2 inhibitor candidate ertugliflozin

Bowles, Paul,Brenek, Steven J.,Caron, Stephane,Do, Nga M.,Drexler, Michele T.,Duan, Shengquan,Dube, Pascal,Hansen, Eric C.,Jones, Brian P.,Jones, Kris N.,Ljubicic, Tomislav A.,Makowski, Teresa W.,Mustakis, Jason,Nelson, Jade D.,Olivier, Mark,Peng, Zhihui,Perfect, Hahdi H.,Place, David W.,Ragan, John A.,Salisbury, John J.,Stanchina, Corey L.,Vanderplas, Brian C.,Webster, Mark E.,Weekly, R. Matt

, p. 66 - 81 (2014/05/20)

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.

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