tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

Base Information

• Chemical Name: tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate
• CAS No.: 154026-95-6
• Molecular Formula: C15H26O6
• Molecular Weight: 302.368
• Hs Code.: 2932999099
• European Community (EC) Number: 688-142-5
• DSSTox Substance ID: DTXSID30934900
• Nikkaji Number: J1.647.738I
• Wikidata: Q72510640
• Mol file: 154026-95-6.mol

Synonyms:154026-95-6;tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate;tert-Butyl 2-((4R,6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;C15H26O6;tert-Butyl 2-[(4R,6S)-6-(Acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate;tert-butyl 2-[(4R,6S)-6-(acetyloxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate;1116473-61-0;[(4S,6R)-6-[2-(tert-butoxy)-2-oxoethyl]-2,2-dimethyl-1,3-dioxan-4-yl]methyl acetate;tert-Butyl 2-(cis-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;MFCD08458213;(4r-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester;SCHEMBL574108;ROSUVASTATIN IMPURITY 91;AMY4201;DTXSID30934900;AC7699;AKOS015896155;AC-3409;CS-W003520;DS-1381;A24820;tert-Butyl 6-O-acetyl-2,4-dideoxy-3,5-O-(1-methylethylidene)hexonate;2-[(4R,6S)-6-(Acetoxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetic acid tert-butyl ester;2-Methyl-2-propanyl 6-O-acetyl-2,4-dideoxy-3,5-O-isopropylidene-D-erythro-hexonate;tert-butyl 2-{(4R,6S)-2,2-dimethyl-6-[(methylcarbonyloxy)methyl]-1,3-dioxan-4-yl}acetate;(4R-cis)-6-[(acetyloxy)methyl]-2 pound not2-dimethyl-
1 pound not3-dioxane-4-acetic acid pound not1 pound not1-dimethylethyl ester;(4R-cis)-6-[(Acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester;Tert-butyl 2-{(4R,6S)-2,2-dimethyl-6-[(methyl-carbonyloxy)methyl]-1,3-dioxan-4-yl}acetate

Chemical Property of tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

Chemical Property:

• Appearance/Colour: White or off-white solid powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.436
• Boiling Point: 353.142 °C at 760 mmHg
• Flash Point: 150.334 °C
• PSA: 71.06000
• Density: 1.037 g/cm³
• LogP: 2.19150
• Storage Temp.: 2-8°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 302.17293854
• Heavy Atom Count: 21
• Complexity: 382

Purity/Quality:

≥98.0% ^*data from raw suppliers

Tert-butyl2-[(4R,6S)-2,2-Dimethyl-6-[(methylcarbonyloxy)methyl]-1,3-dioxan-4-yl]acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1CC(OC(O1)(C)C)CC(=O)OC(C)(C)C
• Isomeric SMILES: CC(=O)OC[C@@H]1C[C@@H](OC(O1)(C)C)CC(=O)OC(C)(C)C
• Uses: Tert-butyl 2-[(4R,6S)-2,2-Dimethyl-6-[(methylcarbonyloxy)methyl]-1,3-dioxan-4-yl]acetate (Rosuvastatin Impurity 19) is an impurity of Rosuvastatin (R700500), a selective and competitive HMG-CoA reductase inhibitor.

Technology Process of tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

There total 25 articles about tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate 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: 99.1%

tetrabutylammonium acetate (10534-59-5) + (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester (154026-94-5,521973-99-9,521974-00-5,521974-01-6) → (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester (154026-95-6)

Guidance literature:

at 115 ℃; for 7h;

Reference yield: 97.6%

sodium acetate (127-09-3) + (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester (154026-94-5,521973-99-9,521974-00-5,521974-01-6) → (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester (154026-95-6)

Guidance literature:

With copper(l) chloride; In N,N-dimethyl-formamide; at 120 - 130 ℃; for 24h; Reagent/catalyst; Solvent;

Reference yield: 95.8%

(3R,5S)-6-acetoxy-3,5-dihydroxyhexanoic acid tert-butyl ester + 2,2-dimethoxy-propane (77-76-9) → (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester (154026-95-6)

Guidance literature:

With methanesulfonic acid; In toluene; at 20 ℃; for 8h;

upstream raw materials:

potassium acetate

(4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester

sodium hydrogencarbonate

2,2-dimethoxy-propane

Downstream raw materials:

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

tert-butyl 2-[(4R,6S)-6-formyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

(4R,6S)-(E)-{6-[2-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-vinyl]-2,2-dimethyl-1,3-dioxan-4-yl}acetic acid tert-butyl ester

[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester

Refernces

• 1、 -. "Preparation method of rosuvastatin intermediate". Paragraph 0025. . Retrieved 2018/10/11.
• 2、 -. "Method for synthesizing ADA". . . Retrieved 2018/02/04.