methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylate

Base Information

• Chemical Name: methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylate
• CAS No.: 174264-49-4
• Molecular Formula: C₄₇H₅₇NO₁₃SSi
• Molecular Weight: 904.12
• DSSTox Substance ID: DTXSID10571695
• Wikidata: Q82459852
• Mol file: 174264-49-4.mol

Synonyms:174264-49-4;methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylate;DTXSID10571695;2-(4-{[tert-Butyl(dimethyl)silyl]oxy}phenyl)-3-{4-[2-(piperidin-1-yl)ethoxy]benzoyl}-1-benzothiophen-6-yl methyl 2,3,4-tri-O-acetyl-beta-D-glucopyranosiduronate;Methyl-1-(4 inverted exclamation mark -tert-butyldimethylsylyl-6-hydroxyraloxifene)-2,3,4-tri-O-acetyl-|A-D-glycopyranuronate;Methyl-1-(4'-tert-butyldimethylsylyl-6-hydroxyraloxifene)-2,3,4-tri-O-acetyl-?-D-glycopyranuronate

Chemical Property of methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylate

Chemical Property:

• PSA: 190.67000
• LogP: 8.05770
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethanol, Methanol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 20
• Exact Mass: 903.33198858
• Heavy Atom Count: 63
• Complexity: 1570

Purity/Quality:

95% ^*data from raw suppliers

Methyl-1-(4’-tert-butyldimethylsylyl-6-hydroxyraloxifene)-2,3,4-tri-O-acetyl-β-D-glycopyranuronate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC(C1OC(=O)C)OC2=CC3=C(C=C2)C(=C(S3)C4=CC=C(C=C4)O[Si](C)(C)C(C)(C)C)C(=O)C5=CC=C(C=C5)OCCN6CCCCC6)C(=O)OC)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@@H]([C@H](O[C@H]([C@@H]1OC(=O)C)OC2=CC3=C(C=C2)C(=C(S3)C4=CC=C(C=C4)O[Si](C)(C)C(C)(C)C)C(=O)C5=CC=C(C=C5)OCCN6CCCCC6)C(=O)OC)OC(=O)C
• Uses: An intermediate in the synthesis for the metabolite of Raloxifene, a nonsteroidal estrogen receptor mixed agonist/antagonist.

Technology Process of methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylate

There total 1 articles about methyl (2S,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[[2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylate 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: 35.0%

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate (3082-96-0,5432-32-6,7355-18-2,19231-41-5,30628-06-9,30628-07-0,40268-90-4,40268-95-9,40269-24-7,104195-05-3,108032-41-3) + 2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone (174264-46-1) → (2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (174264-49-4)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0960-894X(97)00142-X

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (174264-49-4) → 4-[6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]benzothien-2-yl]phenyl-D-glucopyranosiduronicacid (174264-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / dioxane / 60 °C

2: tetrabutylammonium fluoride / tetrahydrofuran

With lithium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0960-894X(97)00142-X

upstream raw materials:

methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate

2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-6-hydroxybenzo[b]thiophen-3-yl 4-[2-(1-piperidinyl)ethoxy]phenyl ketone

Downstream raw materials:

4-[6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]benzothien-2-yl]phenyl-D-glucopyranosiduronicacid