tert-Butyl 2-[(4R,6S)-2,2-Dimethyl-6-[(1-phenyl-1H-terazol-5-ylsulfonyl)methyl]-1,3-dioxan-4-yl]acetate

Base Information

• Chemical Name: tert-Butyl 2-[(4R,6S)-2,2-Dimethyl-6-[(1-phenyl-1H-terazol-5-ylsulfonyl)methyl]-1,3-dioxan-4-yl]acetate
• CAS No.: 380460-37-7
• Molecular Formula: C₂₀H₂₈N₄O₆S
• Molecular Weight: 452.532
• Mol file: 380460-37-7.mol

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

Chemical Property of tert-Butyl 2-[(4R,6S)-2,2-Dimethyl-6-[(1-phenyl-1H-terazol-5-ylsulfonyl)methyl]-1,3-dioxan-4-yl]acetate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 136-138oC
• Boiling Point: 584.9±48.0 °C(Predicted)
• PKA: -0.77±0.10(Predicted)
• Density: 1.34±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%Min ^*data from raw suppliers

tert-Butyl2-[(4R,6S)-2,2-Dimethyl-6-[(1-phenyl-1H-terazol-5-ylsulfonyl)methyl]-1,3-dioxan-4-yl]acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A reagent for Julia coupling. A heterocyclic-substituted dihydroxyheptenoic acid as HMG-CoA reductase inhibitors. (4S,6R)-2,4,6-Trideoxy-3,5-O-(1-methylethylidene)-6-[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]-D-erythro-hexonic Acid 1,1-Dimethylethyl Ester (cas# 380460-37-7) is a compound useful in organic synthesis.

Technology Process of tert-Butyl 2-[(4R,6S)-2,2-Dimethyl-6-[(1-phenyl-1H-terazol-5-ylsulfonyl)methyl]-1,3-dioxan-4-yl]acetate

There total 12 articles about tert-Butyl 2-[(4R,6S)-2,2-Dimethyl-6-[(1-phenyl-1H-terazol-5-ylsulfonyl)methyl]-1,3-dioxan-4-yl]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: 73.0%

[(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazol-5-ylsulfanylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester (380460-39-9) → [(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester (380460-37-7)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 2 - 25 ℃; for 16h;

Reference yield:

(S)-3-hydroxy-4-[(1-phenyltetrazole-5-yl)sulfanyl]butyronitrile (1419874-04-6) → [(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester (380460-37-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine; dmap / dichloromethane / 0 °C

1.2: 0 - 25 °C

2.1: zinc; methanesulfonic acid / tetrahydrofuran / Inert atmosphere; Reflux

2.2: 50 - 60 °C

3.1: diethyl methoxy borane / tetrahydrofuran / 1 h / -70 - -60 °C / Inert atmosphere

3.2: 3 h / -70 - 60 °C / Inert atmosphere

4.1: methanesulfonic acid / acetone / 3 h / 20 °C

5.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 20 - 50 °C

With dmap; ammonium molybdate; methanesulfonic acid; diethyl methoxy borane; dihydrogen peroxide; triethylamine; zinc; In tetrahydrofuran; ethanol; dichloromethane; water; acetone;

Reference yield:

1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → [(4R,6S)-2,2-dimethyl-6-(1-phenyl-1H-tetrazole-5-sulfonylmethyl)[1,3]dioxan-4-yl]acetic acid tert-butyl ester (380460-37-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; sodium iodide / N,N-dimethyl-formamide / 0.5 h / 20 °C

1.2: 90 °C

2.1: toluene / 80 °C

3.1: zinc; methanesulfonic acid / tetrahydrofuran / Inert atmosphere; Reflux

3.2: 50 - 60 °C

4.1: diethyl methoxy borane / tetrahydrofuran / 1 h / -70 - -60 °C / Inert atmosphere

4.2: 3 h / -70 - 60 °C / Inert atmosphere

5.1: methanesulfonic acid / acetone / 3 h / 20 °C

6.1: ammonium molybdate; dihydrogen peroxide / ethanol; water / 20 - 50 °C

With ammonium molybdate; methanesulfonic acid; diethyl methoxy borane; dihydrogen peroxide; triethylamine; sodium iodide; zinc; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetone; toluene;

upstream raw materials:

5-mercapto-1-phenyl-1H-tetrazole sodium salt

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

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

(S)-3-trimethylsiloxy-4-[(1-phenyltetrazole-5-yl)sulfanyl]butyronitrile

Downstream raw materials:

rosuvastatin tert-butyl ester

rosuvastatin

2-[(4R,6S)-6-[(E)-2-[4-(4-fluorophenyl)-2-(N-methylmethanesulfonamido)-6-(isopropyl)pyrimidin-5-yl]vinyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid tert butyl ester

C₂₉H₄₀FN₃O₆S

Refernces

• 1、 -. "PROCESSES FOR THE PREPARATION OF ROSUVASTATIN OR PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF". Page/Page column 25-26. . Retrieved 2016/09/22.
• 2、 -. "AN INTERMEDIATE OF STATIN DRUGS AND PREPARATION THEREOF". Page/Page column 23. . Retrieved 2013/03/26.