(2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 461432-25-7
• Molecular Formula: C29H33ClO10
• Molecular Weight: 577.028
• European Community (EC) Number: 930-010-9
• DSSTox Substance ID: DTXSID50439487
• Mol file: 461432-25-7.mol

Synonyms:461432-25-7;(2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate;[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]oxan-2-yl]methyl acetate;Dapagliflozin Tetraacetate;EC 930-010-9;(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol tetraacetate;(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[4-chloro-3-(4-ethoxybenzyl)phenyl]-D-glucitol;(1S)-2,3,4,6-Tetra-O-acetyl-1,5-anhydro-1-(4-chloro-3-(4-ethoxybenzyl)phenyl)-D-glucitol;(2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)-phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate;Dapagliflozin Tetraacetate ([(2R,3R,4R,5S,6S)-3,4,5-Triacetoxy-6-[4-chloro-3-(4-ethoxybenzyl)phenyl]tetrahydropyran-2-yl]methyl Acetate);C29H33ClO10;MFCD22494949;Hydromorphone N-Oxide Hydrochloride;([(2R,3R,4R,5S,6(S)-3,4,5-Triacetoxy-6-[4-chloro-3-(4-ethoxybenzyl)phenyl]tetrahydropyran-2-yl]methyl Acetate);(1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol 2,3,4,6-tetraacetate;D-Glucitol, 1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-, tetraacetate, (1S)- (9CI);CID 10415783;Tetra acetyl Dapagliflozin;SCHEMBL208112;DTXSID50439487;AMY16480;AKOS015999910;CS-O-14895;AC-30644;DS-17942;CS-0009472;F11505;A897845;(2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-[4-chloro-3-(4-ethoxybenzyl)phenyl]tetrahydropyran-3,4,5-triyl Triacetate;(2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyltriacetate;acetic acid (2R,3R,4R,5S,6S)-3,4,5-triacetoxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of (2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

• Vapor Pressure: 0Pa at 25℃
• Boiling Point: 626.8±55.0 °C(Predicted)
• PSA: 123.66000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 4.12760
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 14
• Exact Mass: 576.1762249
• Heavy Atom Count: 40
• Complexity: 873

Purity/Quality:

99% ^*data from raw suppliers

DapagliflozinTetraacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)Cl
• Isomeric SMILES: CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)Cl
• Uses: Dapagliflozin Tetraacetate is a derivative of Dapagliflozin [D226255], a sodium-glucose transporter 2 inhibitor.

Technology Process of (2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 36 articles about (2R,3R,4R,5S,6S)-2-(Acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

dapagliflozin (461432-26-8,1373321-04-0) + acetic anhydride (108-24-7) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (461432-25-7)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 2h; Cooling with ice;

DOI:10.1021/jacs.7b03781

Reference yield: 84.0%

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene (461432-23-5) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (461432-25-7)

Guidance literature:

4-bromo-1-chloro-2-[(4-ethoxyphenyl)methyl]benzene; With isopropylmagnesium chloride; In tetrahydrofuran; at -5 - 0 ℃; for 2h;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; With N,N,N,N,-tetramethylethylenediamine; isopropylmagnesium chloride; cobalt(II) chloride; In tetrahydrofuran; 2-methyltetrahydrofuran; at 0 - 30 ℃; for 2.5h; Reagent/catalyst; Solvent;

Reference yield: 78.0%

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (461432-25-7)

Guidance literature:

1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene; With isopropylmagnesium chloride; In 2-methyltetrahydrofuran; at -5 - 0 ℃; for 2h;

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide; With N,N,N,N,-tetramethylethylenediamine; isopropylmagnesium chloride; cobalt(III) acetylacetonate; In 2-methyltetrahydrofuran; at 0 - 30 ℃; for 2.5h;

upstream raw materials:

methyl-2,3,4,6-tetra-O-acetyl-1-C-(2-chloro-4'ethoxydiphenylmethan-3yl)-α-D-glucopyranose

(1S)-1,5-anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol

acetic anhydride

1-(5-bromo-2-chlorophenyl)-1-methylethanol

Downstream raw materials:

dapagliflozin

1-{4-chloro-3-[(dimethyl)(4-ethyloxyphenyl)methyl]phenyl}-1-deoxy-β-D-glucopyranose

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

1-C-[4-chloro-3-[[4-[[(3S)-tetrahydro-3-furanyl]oxy]phenyl]methyl]phenyl]-D-glucopyranoside

Refernces

• 1、 -. "PREPARATION OF HIGHLY PURE AMORPHOUS DAPAGLIFLOZIN". Page/Page column 26. . Retrieved 2021/12/13.
• 2、 -. "Preparation method of dapagliflozin". Paragraph 0034; 0035; 0037; 0040; 0041; 0043; 0045; 0046. . Retrieved 2020/05/05.