(4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester

Base Information

• Chemical Name: (4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester
• CAS No.: 154026-94-5
• Molecular Formula: C13H23 Cl O4
• Molecular Weight: 278.776
• DSSTox Substance ID: DTXSID10431508
• Nikkaji Number: J1.647.866K
• Wikidata: Q82245417
• Mol file: 154026-94-5.mol

Synonyms:154026-94-5;(4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester;tert-butyl 2-[(4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate;tert-Butyl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;SCHEMBL573699;DTXSID10431508;MFCD08706402;AKOS015967521;AS-19282;CS-0165342;A854514;J-009061;(4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tBu Ester;(4R)-2,2-Dimethyl-6beta-(chloromethyl)-1,3-dioxane-4beta-acetic acid tert-butyl ester;(4R-ciS)-6-chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid t-butyl ester;tert-Butyl [(4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate;tert-Butyl2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-butyl 2-((4R,6S)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate? (Rosuvastatin Impurity pound(c)

Chemical Property of (4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.439
• Boiling Point: 326.196°C at 760 mmHg
• Flash Point: 113.559°C
• PSA: 44.76000
• Density: 1.046g/cm³
• LogP: 2.86720
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 278.1284869
• Heavy Atom Count: 18
• Complexity: 296

Purity/Quality:

≥98.0% ^*data from raw suppliers

(4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-aceticAcidtert-ButylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(CC(O1)CCl)CC(=O)OC(C)(C)C)C
• Isomeric SMILES: CC1(O[C@H](C[C@H](O1)CCl)CC(=O)OC(C)(C)C)C
• Uses: A HMG-CoA reductase inhibitor intermediate.

Technology Process of (4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester

There total 10 articles about (4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester 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: 98.0%

2,2-dimethoxy-propane (77-76-9) + 1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate (154026-93-4) → (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)

Guidance literature:

With camphor-10-sulfonic acid; In acetone; at 25 ℃; for 1.5h;

DOI:10.1002/1521-3765(20011105)7:21<4562::AID-CHEM4562>3.0.CO;2-4

Reference yield: 81.0%

(4R-cis)-(6-Chloromethyl)-2,2-dimethyl-1,3-dioxane-4-yl-acetic Acid, Sodium Salt (391218-18-1) + tert-butyl alcohol (75-65-0) → (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)

Guidance literature:

(4R-cis)-(6-Chloromethyl)-2,2-dimethyl-1,3-dioxane-4-yl-acetic Acid, Sodium Salt; With 1-methyl-pyrrolidin-2-one; oxalyl dichloride; In toluene; at 20 - 25 ℃; for 6h;

tert-butyl alcohol; With 4-methyl-morpholine; In toluene; for 1h;

With sodium hydroxide; In water; toluene; at 40 ℃; for 1.5h;

Reference yield: 67.0%

2,2-dimethoxy-propane (77-76-9) + tert-butyl (5S)-6-chloro-3,5-dihydroxyhexanoate (406680-96-4) → (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)

Guidance literature:

2,2-dimethoxy-propane; tert-butyl (5S)-6-chloro-3,5-dihydroxyhexanoate; With camphor-10-sulfonic acid; In acetone; at 20 ℃; for 2h;

With hydrogenchloride; In dichloromethane; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/ol017223u

upstream raw materials:

2,2-dimethoxy-propane

1,1-dimethylethyl (3R,5S)-6-chloro-3,5-dihydroxy-4-hexanoate

tert-butyl (5S)-6-chloro-3,5-dihydroxyhexanoate

tert-butyl acetoacetate

Downstream raw materials:

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

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

(3R,5R)-tert-butyl-6-cyano-3,5-dihydroxyhexanoate

Refernces

• 1、 Roy, Bhairab Nath,Singh, Girij Pal,Lathi, Piyush Suresh,Agrawal, Manoj K,Mitra, Rangan. "Stereoselective reduction of δ-hydroxy β-ketoesters to syndiol in achiral micellar system". . p. 1247 - 1251. Retrieved 2015/11/24.
• 2、 -. "PROCESS FOR THE PREPARATION OF DIOXANE ACETIC ACID ESTERS". Page 4. . Retrieved 2010/02/04.