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

Base Information

• Chemical Name: (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester
• CAS No.: 124655-09-0
• Molecular Formula: C13H24O5
• Molecular Weight: 260.331
• Hs Code.: 29329990
• European Community (EC) Number: 432-960-5,684-596-3
• DSSTox Substance ID: DTXSID50431244
• Nikkaji Number: J673.768D
• Wikidata: Q72485209
• Mol file: 124655-09-0.mol

Synonyms:124655-09-0;(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester;tert-Butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate;tert-butyl 2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetate;tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;(4R-cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid-1,1-dimethyethyl ester;MFCD08063915;(4R,6S)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid 1,1-Dimethylethyl Ester;EC 432-960-5;611205-80-2;D-Erythro-hexanoic acid 2,4-dideoxy-3,5-O-(1-methylethylidene)-1,1-dimethylethylester;SCHEMBL247199;AMY4155;DTXSID50431244;AKOS015841510;AKOS015904380;AC-1298;CS-W019118;D-erythro-Hexonic acid, 2,4-dideoxy-3,5-O-(1-methylethylidene)-, 1,1-dimethylethyl ester;AS-15032;B4214;O12099;A805270;Q-102784;T-butyl-(3R,5S)-6-hydroxy3,5-O-isopropylidene3,5-dihydroxyhexanoate;tert-Butyl (3R,5S)-6-hydroxy-3,5-o-iso-propylidene-3,5-dihydroxyhexanoate;tert-Butyl (4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetate;tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate;tert-Butyl(3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate;((4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid t-butyl ester;((4R,6S)-6-Hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)acetic acid tert-butyl ester;(3R,5S)-3,5-[Isopropylidenebis(oxy)]-6-hydroxyhexanoic acid tert-butyl ester;(4R cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl -1,3-dioxane-4-acetate;(4R,6S)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester;(4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2 dimethyl-1,3- dioxane-4-acetate;(4R-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3- dioxane-4-acetate;(4r-cis)-1,1-dimethylethyl 6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate;(4R-cis)-6-(Hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1dimethylethyl ester;(4R-cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid, 1,1-Dimethylethyl Ester;2-[(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic tert-butyl ester;tert-butyl [(4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-yl]acetate;tert-Butyl-2-[(4R,6S)-6-hydroxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl]acetate;(4R-cis)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester;2-[(4R,6S)-6-(HYDROXYMETHYL)-2,2-DIMETHYL-1,3-DIOXAN-4-YL]ACETIC ACID TERT-BUTYL ESTER

Chemical Property of (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.442
• Boiling Point: 330.93 ºC at 760 mmHg
• PKA: 14.25±0.10(Predicted)
• Flash Point: 113 ºC
• PSA: 64.99000
• Density: 1.03 g/cm³
• LogP: 1.62070
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 260.16237386
• Heavy Atom Count: 18
• Complexity: 292

Purity/Quality:

≥98.0% ^*data from raw suppliers

(4R,6S)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-aceticAcid1,1-DimethylethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(CC(O1)CO)CC(=O)OC(C)(C)C)C
• Isomeric SMILES: CC1(O[C@H](C[C@H](O1)CO)CC(=O)OC(C)(C)C)C
• Uses: (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester is a useful synthetic intermediate. A useful synthetic intermediate in the preparation of Rosuvastatin (R700500) and its derivatives

Technology Process of (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester

There total 32 articles about (4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl 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: 100.0%

tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate (151140-38-4) → 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (124655-09-0,407577-54-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; at 31 - 33 ℃; for 5h; under 7600 Torr;

DOI:10.1055/s-1995-4028

Reference yield: 99.0%

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester (154026-95-6) → 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (124655-09-0,407577-54-2)

Guidance literature:

With methanol; In methylamine; at 60 - 70 ℃;

Reference yield: 94.0%

(4R,6S)-6-[t-butoxycarbonylmethyl]-2,2-dimethyl-1,3-dioxane-4-carboxylic acid → 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (124655-09-0,407577-54-2)

Guidance literature:

With borane; sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃; for 1.5h; pH=8; pH-value; Reagent/catalyst; Inert atmosphere;

upstream raw materials:

tert-butyl 2-((4R,6S)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

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

tert-butyl 2-((4R, 6S)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate

tert-butyl 2-((4R,6S)-6-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxane-4-yl)acetate

Downstream raw materials:

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

[(4R,6S)-6-(4-Chloro-benzenesulfonyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

(3R,5S)-6-<(p-tolylsulfonyl)oxy>-3,5-O-isopropylidene-3,5-dihydroxyhexanoic acid tert-butyl ester

[(4R,6S)-6-(4-Bromo-benzenesulfonyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-acetic acid tert-butyl ester

Refernces

• 1、 Nagender Rao,Reddy, Reguri Buchi,Mukkanti,Konda, Venu. "A novel process for synthesis of Rosuvastatin". . p. 1018 - 1022. Retrieved 2017.
• 2、 -. "Preparation method of rosuvastatin calcium intermediate". Paragraph 0050-0060. . Retrieved 2021/07/08.
• 3、 -. "Synthesis method of rosuvastatin calcium side chain key intermediate". Paragraph 0045; 0046. . Retrieved 2018/04/28.